4-(1H-imidazol-1-yl)aniline → 2-[5-(Imidazol-1-yl)-1H-indol-3-yl]ethyl alcohol

HRID 1459712Notes

Reaction equation

HRID 1459712 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N1N=CN(C2C=[C:20]3C(=CC=2)NC=[C:21]3[CH2:27][CH2:28][OH:29])C=1>CS(C)=O>[N:1]1([C:6]2[CH:12]=[C:11]3[C:9](=[CH:8][CH:7]=2)[NH:10][CH:20]=[C:21]3[CH2:27][CH2:28][OH:29])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 3201654-(1H-imidazol-1-yl)anilineHCID 105613091H-Indole-3-ethanol, 5-(4H-1,2,4-triazol-4-yl)-

Product 1

HCID 691011572-[5-(Imidazol-1-yl)-1H-indol-3-yl]ethyl alcohol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared from 4-(imidazol-1-yl)aniline (EP497512) as described for Intermediate 3, δ (360 MHz, D6 -DMSO) 2.87 (2H, t, J=7.2 Hz, CH2), 3.64-3.70 (1H, m, CH2 --OH), 4.61 (1H, t, J=5.3 Hz, OH), 7.08 (1H, s, Ar--H), 7.25-7.27 (2H, m, Ar--H), 7.44 (1H, d, J=8.8 Hz, Ar--H), 7.64 (1H, d, J=2.5 Hz, Ar--H), 7.70 (1H, d, J=2.1 Hz, Ar--H), 8.11 (1H, s, Ar--H), 11.00 (1H, s, NH), m/e 228 (M+1)+.

Sources & evidence

ORD record
ord-c6cd66eaa9c04cce9732d1f926b06a3e
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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