Benzonitrile, 3-(bromomethyl)- → 3-(3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

HRID 593511Notes

Reaction equation

HRID 593511 reaction equation
Cl.[CH3:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.Br[CH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24]>>[CH3:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:23]#[N:24])[C:4]=1[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 445539613-Methyl-2-(3-pyridyl)indole hydrochloride

Product 1

HCID 445543113-(3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

Procedure

3-Methyl-2-pyridin-3-yl-1H-indole hydrochloride (Example 1) and 3-bromomethyl-benzonitrile are processed according to the method described in Example 25 to give 3-(3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile. 1H NMR (400 MHz, MeOD) δ ppm 2.33 (s, 3H), 5.41 (s, 2H), 7.08 (d, J=8.1 Hz, 1H), 7.16 (s, 1H), 7.20 (t, J=7.2 Hz, 1H), 7.27 (ddd, J=7.6, 1.0 Hz, 1H), 7.37 (d, J=5.8 Hz, 1H), 7.38-7.42 (m, 1H), 7.54-7.57 (m, 1H), 7.57 (s, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.85 (dt, J=7.8, 1.9 Hz, 1H), 8.50 (d, J=2.0 Hz, 1H), 8.60 (dd, J=4.8, 1.5 Hz, 1H). HRMS (ESI) m/z 324.1491 [(M+H)+ Calcd for C22H18N3: 324.1501].

Sources & evidence

ORD record
ord-b9a30435e8ac489b9e49882313425cd5
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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