Benzene, (2-bromoethoxy)- → 1-(2-phenoxy-ethyl)-2-pyridin-3-yl-1H-indole-5-carbonitrile

HRID 593532Notes

Reaction equation

HRID 593532 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([C:26]#[N:27])=[CH:21][CH:20]=3)[CH:12]=1>>[O:4]([CH2:3][CH2:2][N:18]1[C:19]2[C:24](=[CH:23][C:22]([C:26]#[N:27])=[CH:21][CH:20]=2)[CH:25]=[C:17]1[C:13]1[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 68526Benzene, (2-bromoethoxy)-HCID 445541352-pyridin-3-yl-1H-indole-5-carbonitrile

Product 1

HCID 582157211-(2-phenoxy-ethyl)-2-pyridin-3-yl-1H-indole-5-carbonitrile

Procedure

(2-Bromo-ethoxy)-benzene and 2-pyridin-3-yl-1H-indole-5-carbonitrile (Example 8) are processed according to the method described in Example 57 to give 1-(2-phenoxy-ethyl)-2-pyridin-3-yl-1H-indole-5-carbonitrile. 1H NMR (400 MHz, MeOD) δ ppm 4.19 (t, J=5.2 Hz, 2H), 4.67 (t, J=5.1 Hz, 2H), 6.63 (d, J=7.8 Hz, 2H), 6.77 (s, 1H), 6.84 (t, J=7.5 Hz, 1H), 7.10-7.17 (m, 2H), 7.53 (dd, J=8.6, 1.8 Hz, 1H), 7.55-7.60 (m, 1H), 7.77 (d, J=8.6 Hz, 1H), 8.05 (s, 1H), 8.08-8.13 (m, 1H), 8.63 (dd, J=4.9, 1.6 Hz, 1H), 8.79 (d, J=1.5 Hz, 1H). HRMS (ESI) m/z 340.1453 [(M+H)+ Calcd for C22H18N3O: 340.1450].

Sources & evidence

ORD record
ord-e84b55adaa4048f99fd62e735ac635ec
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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