1-Methyl-4-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]carbonyl}piperazine → 6-(2,6-Difluoro-3,5-dimethoxyphenyl)-3-{2-[(4-methylpiperazin-1-yl)carbonyl]-2,3-dihydro-1-benzofuran-5-yl}-1H-pyrazolo[4,3-c]pyridine

HRID 1778686Notes

Reaction equation

HRID 1778686 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](I)=[N:20][NH:21][C:15]=2[CH:14]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]([CH:32]2[CH2:36][C:35]3[CH:37]=[C:38](B4OC(C)(C)C(C)(C)O4)[CH:39]=[CH:40][C:34]=3[O:33]2)=[O:31])[CH2:26][CH2:25]1>>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([C:38]3[CH:39]=[CH:40][C:34]4[O:33][CH:32]([C:30]([N:27]5[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]5)=[O:31])[CH2:36][C:35]=4[CH:37]=3)=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 867228111-Methyl-4-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]carbonyl}piperazineHCID 1784934906-(2,6-difluoro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 762852656-(2,6-Difluoro-3,5-dimethoxyphenyl)-3-{2-[(4-methylpiperazin-1-yl)carbonyl]-2,3-dihydro-1-benzofuran-5-yl}-1H-pyrazolo[4,3-c]pyridine

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 4, Step 2 starting from 6-(2,6-difluoro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine and 1-methyl-4-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]carbonyl}piperazine. LCMS (M+H)+=536.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-18901becd9ff4556b0a36a5391f8fdc6
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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