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}-4-chloro-2-methyl-1H-indole-5-carbonitrile

HRID 913601Notes

Reaction equation

HRID 913601 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:13])[NH:6]2.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[O:22][C:23]([CH2:26]Cl)=[N:24][N:25]=2)[CH:20]=1>>[Br:14][C:15]1[CH:20]=[C:19]([C:21]2[O:22][C:23]([CH2:26][N:6]3[C:7]4[C:3](=[C:2]([Cl:1])[C:10]([C:11]#[N:12])=[CH:9][CH:8]=4)[CH:4]=[C:5]3[CH3:13])=[N:24][N:25]=2)[CH:18]=[N:17][CH:16]=1

Participants

3

Reactant 2

HCID 289793653-Bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridineHCID 674048784-chloro-2-methyl-1H-indole-5-carbonitrile

Product 1

HCID 578004911-{[5-(5-Bromo-3-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-4-chloro-2-methyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-methyl-1H-indole-5-carbonitrile and 3-bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridine: 1H NMR (400 MHz, DMSO-d6) δ 9.05 (s, 1 H), 8.94 (s, 1 H), 8.48 (s, 1 H), 7.96 (s, 1 H), 7.85 (d, J=8.5 Hz, 1 H), 7.63 (d, J=8.5 Hz, 1 H), 5.96 (s, 2 H), 2.47 (s, 3 H); MS (ES) m/z 429 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-1451128cad694087b18e3fa749ef956c
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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