(5-Bromothiophen-2-yl)(piperidin-1-yl)methanone → [2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-{4-[5-(piperidine-1-carbonyl)-thiophen-2-yl]-phenyl}-methanone

HRID 646440Notes

Reaction equation

HRID 646440 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1)=[O:14].Br[C:31]1[S:35][C:34]([C:36]([N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:37])=[CH:33][CH:32]=1>>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:31]2[S:35][C:34]([C:36]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[O:37])=[CH:33][CH:32]=2)=[CH:17][CH:16]=1)=[O:14]

Participants

3

Reactant 2

HCID 25236221(5-Bromothiophen-2-yl)(piperidin-1-yl)methanoneHCID 57980025[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Product 1

HCID 11605120[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-{4-[5-(piperidine-1-carbonyl)-thiophen-2-yl]-phenyl}-methanoneYield 48%

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure A using [2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone (550 mg, 1.4 mmol) and (5-Bromo-thiophen-2-yl)-piperidin-1-yl-methanone (CAS 626242-11-3) (315 mg, 1.2 mmol) to give 260 mg (48% yield). MS (ES+) 466.2 (M+H)+

Workup

  1. customto give 260 mg (48% yield)

Sources & evidence

ORD record
ord-d50ba011e3e543fc8b45db885f1835be
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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