4-Aminobenzonitrile → HCID 68843219, compound

HRID 1784868Notes

Reaction equation

HRID 1784868 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH:20]=[CH:21][N:22]3[Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.[NH2:37][C:38]1[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=1>>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][O:8][C:6]2[CH:7]=[C:2]([NH:37][C:38]3[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=3)[CH:3]=[C:4]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[Si:27]([CH:31]([CH3:33])[CH3:32])([CH:34]([CH3:35])[CH3:36])[CH:28]([CH3:29])[CH3:30])[CH:5]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 133964-AminobenzonitrileHCID 50993867HCID 50993867, compound

Product 1

HCID 68843219HCID 68843219, compound

Procedure

4-[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole was coupled with 4-amino-benzonitrile to give 4-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenylamino]-benzonitrile using the conditions of Example 80. This compound was deprotected to give 4-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-benzonitrile as described in Example 35. 1H NMR (400 MHz, CD3OD): δ 7.46 (d, J=2.0 Hz, 1H), 7.45 (d, J=2.0 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.25 (d, J=3.1 Hz, 1H), 7.15-7.11 (m, 3H), 7.06 (dd, J=7.2, 1.0 Hz, 1H), 6.96 (t, J=1.7 Hz, 1H), 6.84 (dd, J=2.1, 1.4 Hz, 1H), 6.66 (t, J=2.1 Hz, 1H), 6.62 (q, J=1.4 Hz, 1H).

Sources & evidence

ORD record
ord-8868586ea3dd4717b90f394488669e67
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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