Methyl iodide → (R)-tert-Butyl 2-(5-bromo-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate

HRID 1481717Notes

Reaction equation

[CH3:1]C([O-])(C)C.[K+].CI.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[C:17]#[C:18][C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>>[Br:16][C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[N:9]([CH3:1])[C:18]([C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:17]2

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 23665647Potassium tert-butoxide

HCID 117844394(R)-tert-butyl 2-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylate

Product 1

HCID 71284656(R)-tert-Butyl 2-(5-bromo-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylateYield 78%

Procedure

(R)-tert-Butyl 2-(5-bromo-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate (3.245 g) was prepared via t-BuOK cyclization/MeI alkylation sequence described in Example 156, Step 2, from (R)-tert-butyl 2-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylate (3.989 g, 10.92 mmol) in 78% yield.

Sources & evidence

ORD record: ord-d3c2629125ae440fa4429a2278c5601f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

Loading…