3-(2-Bromoethyl)indole → HCID 59489562, compound

HRID 1879213Notes

Reaction equation

HRID 1879213 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13]([C:15]3[NH:16][N:17]=[CH:18][CH:19]=3)=[N:12][C:11]=2[CH3:20])=[O:9])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1>>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13]([C:15]3[CH:19]=[CH:18][N:17]([CH2:24][CH2:25][C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[NH:28][CH:27]=4)[N:16]=3)=[N:12][C:11]=2[CH3:20])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 769243-(2-Bromoethyl)indoleHCID 68489655HCID 68489655, compound

Product 1

HCID 59489562HCID 59489562, compound

Procedure

The title compound was prepared from 4-methyl-2-(2H-pyrazol-3-yl)thiazole-5-carboxylic acid 4-fluoro-benzylamide and 3-(2-bromo-ethyl)-1H-indole as describe in Example 83 and isolated as a yellow solid (0.056 g, 40% yield). 1H NMR (400 MHz, CDCl3) δ 8.01 (bs, 1H), 7.56 (d, J=8 Hz, 1H), 7.31-7.38 (m, 2H), 7.20-7.25 (m, 1H), 7.10-7.16 (m, 2H), 6.81 (d, J=2 Hz, 1H), 6.70 (d, J=2 Hz, 1H), 5.99-6.04 (m, 1H), 4.59 (d, J=4 Hz, 2H), 4.45 (t, J=7 Hz, 2H), 3.35 (t, J=7 Hz, 2H), 2.76 (s, 3H); MS (M+H)+=460.2; Rt=1.47 min; HRMS (M+H)+=460.16.

Sources & evidence

ORD record
ord-3d3c1dfa84e645f098951390bb34c5c8
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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