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 → {2-Fluoro-4-[5-(pyrrolidine-1-carbonyl)-thiazol-2-yl]-phenyl}-[2-(S)-(2-(R)-methyl pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 646447Notes

Reaction equation

HRID 646447 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]([C:37]([N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[O:38])=[CH:35][N:36]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:32]2[S:33][C:34]([C:37]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:38])=[CH:35][N: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 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 591740852-Bromo-5-(pyrrolidine-1-carbonyl)-1,3-thiazole

Product 1

HCID 59264679{2-Fluoro-4-[5-(pyrrolidine-1-carbonyl)-thiazol-2-yl]-phenyl}-[2-(S)-(2-(R)-methyl pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanoneYield 32%

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 (354 mg, 0.85 mmol) and (2-bromo-thiazol-5-yl)-pyrrolidin-1-yl-methanone (222 mg, 0.85 mmol) to give 130 mg (32% yield). MS (ES+) 471.3 (M+H)+

Workup

  1. customto give 130 mg (32% yield)

Sources & evidence

ORD record
ord-531bb386ae1948d4b5a5aca0f17830ef
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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