2-Bromo-5-methanesulfonylthiophene → [2-Fluoro-4-(5-methanesulfonyl-thiophen-2-yl)-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 646443Notes

Reaction equation

HRID 646443 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH3:30])=[O:18].Br[C:32]1[S:33][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][CH:36]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:32]2[S:33][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][CH:36]=2)[CH:5]=[CH:4][C:3]=1[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH3:30])=[O:18]

Participants

3

Reactant 2

HCID 173902812-Bromo-5-methanesulfonylthiopheneHCID 579800402-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

Product 1

HCID 59264696[2-Fluoro-4-(5-methanesulfonyl-thiophen-2-yl)-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanoneYield 78%

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure A using [2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone (458 mg, 1.1 mmol) and 2-Bromo-5-methanesulfonyl-thiophene (CAS 2160-61-4) (255 mg, 1.0 mmol) to give 350 mg (78% yield). MS (ES+) 451.2 (M+H)+

Workup

  1. customto give 350 mg (78% yield)

Sources & evidence

ORD record
ord-4b73507070094a359e229cd324291074
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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