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

HRID 913518Notes

Reaction equation

HRID 913518 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:14])([F:13])[F:12])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2.Br[CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([F:27])=[N:25][CH:26]=1>>[F:27][C:24]1[N:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][N:3]2[C:4]3[C:9](=[C:8]([C:11]([F:12])([F:14])[F:13])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrileHCID 67405380Pyridine, 5-(2-bromoethoxy)-2-fluoro-

Product 1

HCID 674048531-{2-[(6-Fluoro-3-pyridinyl)oxy]ethyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 using 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile and 5-[(2-bromoethyl)oxy]-2-fluoropyridine. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (d, J=8.5 Hz, 1H), 7.76 (s, 1H), 7.69 (d, J=8.5 Hz, 1H), 7.45 (m, 1H), 7.03 (dd, J=9.0 and 3.4 Hz, 1H), 6.54 (s, 1H), 4.69 (t, J=5.1 Hz, 2H), 4.35 (t, J=5.1 Hz, 2H), 2.56 (s, 3H); MS (ES) m/z 364 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-02415d6f622c425f8cb141e5a044a39d
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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