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

HRID 646430Notes

Reaction equation

HRID 646430 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:7]#[N:8])[S:5][CH:6]=1.[CH3:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][CH:24]=1)=[O:22]>>[CH3:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[C:4]([C:7]#[N:8])[S:5][CH:6]=2)=[CH:25][CH:24]=1)=[O:22]

Participants

3

Reactant 2

HCID 142923554-Bromothiophene-2-carbonitrileHCID 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 115670734-{4-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidine-1-carbonyl]-phenyl}-thiophene-2-carbonitrile

Procedure

The title compound is prepared in a manner substantially analogous General Procedure A using 4-bromo-thiophene-2-carbonitrile (CAS 18791-99-6) and [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 to give the title compound. (150 mg, 30% yield). MS (ES+) 380.2 (M+H)+

Sources & evidence

ORD record
ord-ffdd8ed63ed14c3195191cf60e78ba60
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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