6-Fluoropyridin-3-ol → 1-{2-[(6-Fluoro-3-pyridinyl)oxy]propyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2102166Notes

Reaction equation

HRID 2102166 reaction equation
[OH:1][CH:2]([CH3:20])[CH2:3][N:4]1[C:12]2[C:7](=[C:8]([C:15]([F:18])([F:17])[F:16])[C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH:6]=[C:5]1[CH3:19].[F:21][C:22]1[N:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1>>[F:21][C:22]1[N:27]=[CH:26][C:25]([O:1][CH:2]([CH3:20])[CH2:3][N:4]2[C:12]3[C:7](=[C:8]([C:15]([F:18])([F:16])[F:17])[C:9]([C:13]#[N:14])=[CH:10][CH:11]=3)[CH:6]=[C:5]2[CH3:19])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 27631086-Fluoropyridin-3-olHCID 674038091-(2-Hydroxypropyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 674043101-{2-[(6-Fluoro-3-pyridinyl)oxy]propyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 139C using 1-(2-hydroxypropyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 335) and 6-fluoro-3-pyridinol: 1H NMR (400 MHz, CDCl3) δ 7.58 (s, 1H), 7.54 (d, J=8.6 Hz, 1H), 7.49 (d, J=8.6 Hz, 1H), 6.94 (m, 1H), 6.71 (m, 1H), 6.56 (s, 1H), 4.57 (m, 1H), 4.40 (m, 1H), 4.30 (m, 1H), 2.54 (s, 3H), 1.43 (d, J=6.1 Hz, 3H); MS (ES) m/z 400 (M+Na).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-77d8530852d947869043b3d722ab315b
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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