4-Iodobenzonitrile → 4-(1-acetyl-1H-indol-2-yl)benzonitrile

HRID 1452739Notes

Reaction equation

I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:21])[CH3:20])#[CH:11]>>[C:19]([N:18]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[C:11]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)(=[O:21])[CH3:20]

Participants

Reactant 2

HCID 764674-Iodobenzonitrile

HCID 10261360N-(2-ethynylphenyl)acetamide

Product 1

HCID 251597884-(1-acetyl-1H-indol-2-yl)benzonitrileYield 36%

Procedure

The general procedure was used to convert 4-iodobenzonitrile and N-(2-ethynylphenyl)acetamide to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 36% yield. 1H NMR (300 MHz, DMSO) δ 8.16-8.13 (d, J=8.4, 1H), 7.95-7.92 (d, J=8.6, 2H), 7.76-7.73 (d, J=8.4, 2H), 7.67-7.65 (d, J=7.7, 1H), 7.42-7.36 (dt, J=7.3, 1.5, 1H), 7.33-7.28 (dt, J=7.7, 1.1, 1H) 6.94 (s, 1H), 2.28 (s, 3H). 13C NMR (75 MHz, DMSO) δ 171.42, 139.15, 139.09, 137.98, 133.23, 130.31, 129.57, 126.25, 124.40, 121.99, 119.54, 116.08, 113.63, 111.49, 28.56. Anal. Calcd. for C17H12N2O: C, 78.44; H, 4.65; N, 10.76. Found C, 78.19; H, 4.63; N, 10.68. m.p.: 158-160° C.

Sources & evidence

ORD record: ord-82c51d647c594b939df947a3ab325148
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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