4-Amino-3-iodobenzonitrile → 2-(4-methoxy-pyridin-3-yl)-1H-indole-5-carbonitrile

HRID 593572Notes

Reaction equation

HRID 593572 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]#[CH:10].[C:11]([C:13]1[CH:19]=[C:18](I)[C:16]([NH2:17])=[CH:15][CH:14]=1)#[N:12]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[NH:17][C:16]2[C:18]([CH:10]=1)=[CH:19][C:13]([C:11]#[N:12])=[CH:14][CH:15]=2

Participants

3

Reactant 2

HCID 44163954-Amino-3-iodobenzonitrileHCID 582157063-Ethynyl-4-methoxypyridine

Product 1

HCID 582156342-(4-methoxy-pyridin-3-yl)-1H-indole-5-carbonitrile

Procedure

4-Methoxy-3-ethynyl-pyridine and 4-cyano-6-iodoaniline are processed according to the method described in Example 86 to give 2-(4-methoxy-pyridin-3-yl)-1H-indole-5-carbonitrile. 2-(4-Methoxy-pyridin-3-yl)-1H-indole-5-carbonitrile is purified by HPLC using an Xbridge Shield RP18 with a gradient of acetonitrile in 0.1% NH4OH. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.04 (s, 3H), 7.14 (d, J=1.3 Hz, 1H), 7.25 (d, J=5.8 Hz, 1H), 7.47 (dd, J=8.5, 1.6 Hz, 1H), 7.61 (d, J=8.3 Hz, 1H), 8.11 (s, 1H), 8.47 (d, J=5.8 Hz, 1H), 8.91 (s, 1H), 11.91 (br. s., 1H). HRMS (ESI) m/z 250.0968 [(M+H)+ calcd for C15H12N3O: 250.0980].

Sources & evidence

ORD record
ord-dc9de4c4ce5b4d029179ce744c58defe
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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