cas 219943-38-1, 3,4-DIBROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER | Articles data ｜lookchem

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219943-38-1

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Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.
[reaction: see text] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields.
Chauder, Brian,Larkin, Andrew,Snieckus, Victor
p. 815 - 817
(2007/10/03)

Enantiospecific synthesis of (r)-4-amino-5-oxo-1,3,4,5- tetrahydrobenz[cd]indole, an advanced intermediate containing the tricyclic core of the ergots
We report a new strategy for the enantiospecific synthesis of (R)-4- amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole. This compound is an advanced intermediate which contains the tricyclic core of many of the tetracyclic ergot alkaloids. Our method involves the initial synthesis of D-4- bromotryptophan from the coupling of an indolyllithium species with a masked serinal. The α-amino position was protected with an N-trityl group, ensuring the enantiomeric integrity of this position during the ensuing organometallic cyclization reaction. Stabilization of the tricycle was accomplished by protecting the indole nitrogen with a BOC group or by reducing the α-amino ketone to the corresponding β-amino alcohol.
Hurt, Clarence R.,Lin, Ronghui,Rapoport, Henry
p. 225 - 233
(2007/10/03)

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Chemical Properties

Boiling Point: 414.518 °C at 760 mmHg
Flash Point:204.494 °C
Density: 1.64g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.608
PSA: 31.23000
LogP: 4.94950

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