3-Bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridine → 1-{[5-(5-Bromo-3-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-2-(2-methylpropyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 1188482

Reaction equation

HRID 1188482 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2.[Br:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([C:27]2[O:28][C:29]([CH2:32]Cl)=[N:30][N:31]=2)[CH:26]=1>>[Br:20][C:21]1[CH:26]=[C:25]([C:27]2[O:28][C:29]([CH2:32][N:5]3[C:6]4[C:11](=[C:10]([C:13]([F:16])([F:14])[F:15])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=4)[CH:12]=[C:4]3[CH2:3][CH:2]([CH3:19])[CH3:1])=[N:30][N:31]=2)[CH:24]=[N:23][CH:22]=1

Participants

3

Reactant 2

HCID 289793653-Bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridineHCID 674051962-(2-methylpropyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 674069711-{[5-(5-Bromo-3-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-2-(2-methylpropyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 using 2-(2-methylpropyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile and 3-bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridine: 1H NMR (400 MHz, CDCl3) δ 9.04 (d, J=1.4 Hz, 1H), 8.84 (d, J=2.0 Hz, 1H), 8.43 (m, 1H), 7.68 (d, J=8.4 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 6.67 (s, 1H), 5.63 (s, 2H), 2.82 (d, J=7.1 Hz, 2H), 2.13 (m, 1H), 1.08 (d, J=6.6 Hz, 6H); MS (ES) m/z 504 (M+1, isotope for Br) and 506 (M+1, isotope for Br).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-35e5d8601d1c452c9614151d61f2c75d
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Linked notes

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