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 → [4-(5-Ethanesulfonyl-thiophen-2-yl)-2-fluoro-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 646444Notes

Reaction equation

HRID 646444 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]([CH2:40][CH3:41])(=[O:39])=[O:38])=[CH:35][CH:36]=1>>[CH2:40]([S:37]([C:34]1[S:33][C:32]([C:6]2[CH:5]=[CH:4][C:3]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][C@H:26]3[CH3:30])=[O:18])=[C:2]([F:1])[CH:7]=2)=[CH:36][CH:35]=1)(=[O:39])=[O:38])[CH3:41]

Participants

3

Reactant 2

HCID 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]-methanoneHCID 592646582-Bromo-5-ethanesulfonyl-thiophene

Product 1

HCID 59264699[4-(5-Ethanesulfonyl-thiophen-2-yl)-2-fluoro-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanoneYield 35%

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-ethanesulfonyl-thiophene (255 mg, 1.0 mmol) to give 165 mg (35% yield). MS (ES+) 465.2 (M+H)+

Workup

  1. customto give 165 mg (35% yield)

Sources & evidence

ORD record
ord-bd952615e3d54a0da1dbb3e5e2643e52
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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