9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one

Base Information

• Chemical Name: 9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one
• CAS No.: 1438383-89-1
• Molecular Formula: C19H14Br2O3
• Molecular Weight: 450.126
• Mol file: 1438383-89-1.mol

Synonyms:9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one;9-Bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one;9-Bromo-3-(2-bromo-acetyl)-10,11-dihydro-5H,9H-6-oxa-benzo[a]anthracen-8-one

Chemical Property of 9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one

Chemical Property:

• Boiling Point: 610.2±55.0 °C(Predicted)
• PSA: 43.37000
• Density: 1.734±0.06 g/cm3(Predicted)
• LogP: 4.71600

Purity/Quality:

95% ^*data from raw suppliers

9-Bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 9-Bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one is an antiviral agent and Velpatasvir (V116000) intermediate. Velpatasvir is a NS5A inhibitor in patients with hepatitis C (HCV) infection.

Technology Process of 9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one

There total 2 articles about 9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4'-amino-3'-methyl-acetophenone (43230-11-1) → 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one (1438383-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -10 - -5 °C

1.2: 2 h / 70 °C

2.1: N-Bromosuccinimide / chloroform / 5 h / 70 °C

3.1: potassium carbonate / acetonitrile; benzene / 20 - 60 °C

4.1: potassium carbonate; triphenylphosphine; palladium diacetate; Trimethylacetic acid / N,N-dimethyl acetamide / 2 h / 65 °C / Inert atmosphere

5.1: 3,4,5-tribromopyridine / methanol; dichloromethane / 20 °C

With hydrogenchloride; N-Bromosuccinimide; 3,4,5-tribromopyridine; palladium diacetate; potassium carbonate; triphenylphosphine; sodium nitrite; Trimethylacetic acid; In methanol; dichloromethane; chloroform; N,N-dimethyl acetamide; water; acetonitrile; benzene;

Reference yield:

7-hydroxy-1-tetralone (22009-38-7) → 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one (1438383-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C

2.1: Trimethylacetic acid; potassium carbonate; palladium(II) trimethylacetate; P(p-C₆H₄F)3 / N,N-dimethyl acetamide / 24 h / 60 °C / Inert atmosphere

3.1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate / propan-1-ol / 5.5 h / Inert atmosphere; Reflux

4.1: N-Bromosuccinimide / water; tetrahydrofuran; dimethyl sulfoxide / 0.55 h / 20 °C

4.2: 15 h / 20 °C

5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 3 h / 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; N-Bromosuccinimide; pyridinium hydrobromide perbromide; palladium(II) trimethylacetate; palladium diacetate; potassium carbonate; P(p-C₆H₄F)3; Trimethylacetic acid; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield: 86.0%

9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one (1438383-89-1) + (2S,4S)-1-(benzoyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid + C13H22N2O5 → C46H51N3O12

Guidance literature:

9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one; (2S,4S)-1-(benzoyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid; With caesium carbonate; In tetrahydrofuran; at 20 - 55 ℃;

C₁₃H₂₂N₂O₅; In tetrahydrofuran; at 30 - 55 ℃;

upstream raw materials:

7-hydroxy-1-tetralone

4'-amino-3'-methyl-acetophenone

Downstream raw materials:

(2S,5S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 5-methylpyrrolidine-1,2-dicarboxylate

(2S,4S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

(2R,4R)-1-tert-butyl 2-(2-(9-((2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

Refernces

• 1、 -. "Preparation method of velpatasvir intermediate". . . Retrieved 2018/01/17.
• 2、 -. "ANTIVIRAL COMPOUNDS". . . Retrieved 2014/07/08.