(1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one

Base Information

• Chemical Name: (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one
• CAS No.: 1247001-86-0
• Molecular Formula: C₁₈H₁₄IN₃O₂
• Molecular Weight: 431.233
• Mol file: 1247001-86-0.mol

Synonyms:(1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one

Chemical Property of (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one

There total 1 articles about (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-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:

6-bromo-1H-indazole (79762-54-2) → (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one (1247001-86-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 0.17 h

1.2: 12 h / 20 - 150 °C

2.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 7 h / 80 °C / Inert atmosphere

3.1: potassium carbonate; potassium osmate(VI) dihydrate; potassium hexacyanoferrate(III); 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine / water; tert-butyl alcohol / 6 h / 0 - 10 °C

4.1: triethylamine / dichloromethane / 0.5 h / 0 - 11 °C

5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C

5.2: 2 h / 0 °C

6.1: potassium tert-butylate; oxygen / dimethyl sulfoxide; tetrahydrofuran / 0 - 20 °C

7.1: potassium carbonate / methanol; N,N-dimethyl-formamide / 6 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; potassium osmate(VI) dihydrate; potassium tert-butylate; oxygen; sodium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm5005336

Reference yield: 79.0%

(E)-N,N-dimethyl-1-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanamine (1247001-30-4) + (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one (1247001-86-0) → (1R,2S)-(E)-2-(3-(4-((dimethylamino)methyl)styryl)-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one hydrochloride (1338805-99-4)

Guidance literature:

(E)-N,N-dimethyl-1-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanamine; (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; toluene; at 125 ℃; for 2h; Microwave irradiation;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.666667h;

DOI:10.1021/jm5005336

Reference yield: 61.0%

(E)-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzyl)morpholine (933986-62-0) + (1R,2S)-2-(3-iodo-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one (1247001-86-0) → (1R,2S)-(E)-5'-methoxy-2-(3-(4-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro(cyclopropane-1,3'-indolin)-2'-one (1247002-45-4)

Guidance literature:

With sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 100 ℃; for 18h; Inert atmosphere;

upstream raw materials:

6-bromo-1H-indazole

Downstream raw materials:

(1R,2S)-(E)-5'-methoxy-2-(3-(4-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro(cyclopropane-1,3'-indolin)-2'-one

(1R,2S)-5'-methoxy-2-(3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

(1R,2S)-(E)-5'-methoxy-2-(3-(4-(2-morpholinoethyl)styryl)-1H-indazol-6-yl)spiro(cyclopropane-1,3'-indolin)-2'-one

(1R,2S)-5'-methoxy-2-(3-(4-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one hydrochloride

Refernces