1-Chloro-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile → HCID 58362619, compound

HRID 2361501Notes

Reaction equation

HRID 2361501 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Cl[C:12]1[N:20]2[C:16](=[N:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=32)[C:15]([C:25]#[N:26])=[C:14]([CH3:27])[CH:13]=1>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[N:20]3[C:16](=[N:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=43)[C:15]([C:25]#[N:26])=[C:14]([CH3:27])[CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3558761-Chloro-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrileHCID 27346154-Aminophenylboronic acid

Product 1

HCID 58362619HCID 58362619, compound

Procedure

General experimental procedure (A) for Suzuki coupling reaction with 4-aminophenyl boronic acid was followed. Reaction was performed on a 241 mg scale of 1-chloro-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile. Isolated 100 mg (34%) of T672 as a yellow solid. NMR (CD3OD): δ 7.85 (1H, d, J=8.4 Hz), 7.66 (1H, m), 7.43 (2H, m), 7.26-7.30 (2H, m, overlapped), 7.07 (1H, d, J=8.4 Hz), 7.38 (1H, dd, J=9.0, 2.6 Hz), 6.97 (2H, m), 2.80 (3H, s); MS: 299 (M+H+).

Workup

  1. customReaction
  2. customIsolated 100 mg (34%) of T672 as a yellow solid

Sources & evidence

ORD record
ord-489220667a7e47fc9b16e7d7d8a68028
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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