2-(4-Methylpiperazino)pyrimidine-5-boronic acid pinacol ester → 4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-2-[2-(4-methyl-1-piperazinyl)-5-pyrimidinyl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 29010Notes

Reaction equation

HRID 29010 reaction equation
I[C:2]1[N:25]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=[CH:8][C:9]([C:10]3[C:11]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=4)=[N:12][N:13]([CH3:15])[CH:14]=3)=[C:4]2[CH:3]=1.[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:42]2[N:47]=[CH:46][C:45](B3OC(C)(C)C(C)(C)O3)=[CH:44][N:43]=2)[CH2:38][CH2:37]1>>[CH3:15][N:13]1[CH:14]=[C:10]([C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[N:25]([S:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)(=[O:27])=[O:28])[C:2]([C:45]4[CH:44]=[N:43][C:42]([N:39]5[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]5)=[N:47][CH:46]=4)=[CH:3][C:4]=23)[C:11]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:12]1

Participants

3

Reactant 2

HCID 164142282-(4-Methylpiperazino)pyrimidine-5-boronic acid pinacol esterHCID 689970402-iodo-4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 689971724-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-2-[2-(4-methyl-1-piperazinyl)-5-pyrimidinyl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Procedure

Following the procedure described for Intermediate 241 using 2-iodo-4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine and 2-(4-methyl-1-piperazinyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine provided the title compound. ESMS [M+H]+: 636.0.

Sources & evidence

ORD record
ord-8df46669d03e4572acdd30b45a6a183f
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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