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-propyl-1H-indole-5-carbonitrile

HRID 2102030Notes

Reaction equation

HRID 2102030 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]([CH2:13][CH2:14][CH3:15])[NH:6]2.[Br:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21]([C:23]2[O:24][C:25]([CH2:28]Cl)=[N:26][N:27]=2)[CH:22]=1>>[Br:16][C:17]1[CH:22]=[C:21]([C:23]2[O:24][C:25]([CH2:28][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[CH2:13][CH2:14][CH3:15])=[N:26][N:27]=2)[CH:20]=[N:19][CH:18]=1

Participants

3

Reactant 2

HCID 289793653-Bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridineHCID 674043384-chloro-2-propyl-1H-indole-5-carbonitrile

Product 1

HCID 578004081-{[5-(5-Bromo-3-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-4-chloro-2-propyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-propyl-1H-indole-5-carbonitrile and 3-bromo-5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridine: 1H NMR (400 MHz, DMSO-d6) δ 9.03 (d, J=1.3 Hz, 1H), 8.94 (d, J=2.0 Hz, 1H), 8.46 (s, 1H), 7.97 (s, 1H), 7.81 (d, J=8.5 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 5.96 (s, 2H), 2.95-2.87 (m, 2H), 1.75-1.48 (m, 2H), 0.93 (t, J=7.3 Hz, 3H); MS (ES) m/z 457 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-84168b3af20444f18374466135d53302
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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