3-Bromothiophene-2-carbonitrile → 3-[3-(6(Furan-3-yl)imidazo[4,5-b]pyridin-3-yl)phenyl]thiophene-2-carbonitrile

HRID 2086088Notes

Reaction equation

HRID 2086088 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]3[N:14]=[CH:13][N:12]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17](B5OC(C)(C)C(C)(C)O5)[CH:16]=4)[C:9]3=[N:10][CH:11]=2)=[CH:2]1.Br[C:31]1[CH:35]=[CH:34][S:33][C:32]=1[C:36]#[N:37]>>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]3[N:14]=[CH:13][N:12]([C:15]4[CH:16]=[C:17]([C:31]5[CH:35]=[CH:34][S:33][C:32]=5[C:36]#[N:37])[CH:18]=[CH:19][CH:20]=4)[C:9]3=[N:10][CH:11]=2)=[CH:2]1

Participants

3

Reactant 2

HCID 27400883-Bromothiophene-2-carbonitrileHCID 227279576-(furan-3-yl)-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3H-imidazo[4,5-b]pyridine

Product 1

HCID 227279523-[3-(6(Furan-3-yl)imidazo[4,5-b]pyridin-3-yl)phenyl]thiophene-2-carbonitrile

Procedure

The title compound was prepared from 6-(furan-3-yl)-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3H-imidazo[4,5-b]pyridine and 3-bromothiophene-2-carbonitrile as described in Example 8 to afford the free base as a tan sold; δH (400 MHz, d6-DMSO) 7.17 (1H, s), 7.70 (1H, d, J 5), 7.78-7.86 (3H, m), 8.15 (1H, d, J 8), 8.20 (1H, d, J 5), 8.36-8.37 (2H, m), 8.50 (1H, d, J 2), 8.78 (1H, d, J 2), 9.02 (1H, s); m/z (ES+) 369 (M++H).

Workup

  1. customto afford the free base as a tan

Sources & evidence

ORD record
ord-d8eb379cd42e4be0a66f2eae59276b2d
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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