[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 → 5-{4-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidine-1-carbonyl]-phenyl}-thiophene-3-carbonitrile

HRID 646445Notes

Reaction equation

HRID 646445 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].I[C:31]1[S:35][CH:34]=[C:33]([C:36]#[N:37])[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:16]=[CH:17][C:18]([C:31]2[S:35][CH:34]=[C:33]([C:36]#[N:37])[CH:32]=2)=[CH:19][CH:20]=1)=[O:14]

Participants

3

Reactant 2

HCID 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]-methanoneHCID 685460255-Iodo-3-thiophenecarbonitrile

Product 1

HCID 575801845-{4-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidine-1-carbonyl]-phenyl}-thiophene-3-carbonitrileYield 30%

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 (351 mg, 0.88 mmol) and 5-Iodo-thiophene-3-carbonitrile (CAS 18800-02-7) (165 mg, 0.88 mmol) to give 100 mg (30% yield). MS (ES+) 380.2 (M+H)+

Workup

  1. customto give 100 mg (30% yield)

Sources & evidence

ORD record
ord-de5085181c404e8ea865a492a82166dd
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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