3-Cyanopyridine → 5-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazole

HRID 42321Notes

Reaction equation

HRID 42321 reaction equation
C(N1C(C2C=CC=CC=2)=CN=C1)C1C=CC=CC=1.Br[C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH3:31].[CH2:32]([N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(C1C=NC=CC=1)#N.B(O)(O)C1C=CC=C(F)C=1>ClCCl.CO>[CH2:32]([N:39]1[C:43]([C:20]2[S:24][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:22][C:21]=2[CH3:31])=[CH:42][N:41]=[C:40]1[C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[CH2:32]([N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 5

HCID 793-CyanopyridineHCID 27339863-Fluorophenylboronic acidHCID 27954945-Bromo-4-methyl-2-phenyl-1,3-thiazoleHCID 104440381-benzyl-5-phenyl-1H-imidazoleHCID 673615683-(1-benzyl-1H-imidazol-2-yl)pyridine

Product 2

HCID 592524745-(1-benzyl-2-(pyridin-3-yl)-1H-imidazol-5-yl)-4-methyl-2-phenylthiazoleHCID 673615683-(1-benzyl-1H-imidazol-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the method described in Example 1, except that (i) commercially available 5-bromo-4-methyl-2-phenylthiazole (Apollo Scientific) was used instead of 5-bromo-2-phenylpyrimidine in Step C, and (ii) 3-(1-benzyl-1H-imidazol-2-yl)pyridine was used instead of 1-benzyl-2-phenyl-1H-imidazole in Step C. 3-(1-Benzyl-1H-imidazol-2-yl)pyridine was prepared by the procedure described in Example 8, Steps A and B except the commercially available 3-cyanopyridine was used instead of 3-fluorobenzonitrile; Rf 0.34 with 95:5 v/v dichloromethane-methanol; 1H-NMR (400 MHz; DMSO-d6) δ 8.87 (dd, 1H), 8.64-8.63 (dd, 1H), 7.94-7.91 (m, 1H), 7.86-7.84 (m, 2H), 7.43-7.22 (m, 8H), 6.83-6.81 (m, 2H), 5.25 (s, 2H), 2.31 (s, 3H); MS (ESI+) m/z 409.1 (M+1); H-PGDS FPBA IC50: >20 μM.

Sources & evidence

ORD record
ord-09f15179524547498be191e4abe1b510
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Reaction notes

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