3-Cyanophenylboronic acid → 3-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl} benzonitrile

HRID 1792525Notes

Reaction equation

HRID 1792525 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:23]([C:24]3[CH:25]=[CH:26][C:27]4[N:28]([C:30](I)=[CH:31][N:32]=4)[CH:29]=3)=[CH:22][N:21]([C:34]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:20]=2)=[CH:15][CH:14]=1>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:23]([C:24]3[CH:25]=[CH:26][C:27]4[N:28]([C:30]([C:7]5[CH:8]=[C:3]([CH:4]=[CH:5][CH:6]=5)[C:1]#[N:2])=[CH:31][N:32]=4)[CH:29]=3)=[CH:22][N:21]([C:34]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:20]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 220310706-[3-(4-fluorophenyl)-1-trityl-1H-pyrazolyl]-3-iodoimidazo[1,2-a]pyridine

Product 1

HCID 867601673-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl} benzonitrileYield 87.8%

Procedure

46 mg 3-cyanophenylboronic acid and 161 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 39) were reacted in the same manner as in Example 3, to give 136 mg 3-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl} benzonitrile as colorless crystals. This product was subjected to deprotection of the trityl group and converted into the corresponding hydrochloride by the same method as in Example 68, to give 90 mg of the title compound as colorless crystals.

Sources & evidence

ORD record
ord-cd4666a33ca84b58a1bda57659621282
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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