2-Chloropyridine-4-boronic acid → [6-Bromo-1-(2-chloro-pyridin-4-yl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 19889Notes

Reaction equation

HRID 19889 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:13]3[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15][CH2:14]3)=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:21][CH:22]1[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]1.[Cl:31][C:32]1[CH:37]=[C:36](B(O)O)[CH:35]=[CH:34][N:33]=1>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:13]3[CH2:18][CH2:17][C:16]([F:19])([F:20])[CH2:15][CH2:14]3)=[O:12])[N:8]2[C:36]2[CH:35]=[CH:34][N:33]=[C:32]([Cl:31])[CH:37]=2)=[CH:4][C:3]=1[O:21][CH:22]1[CH2:23][CH2:24][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 51515952-Chloropyridine-4-boronic acidHCID 67017928[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Product 1

HCID 16739660[6-Bromo-1-(2-chloro-pyridin-4-yl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described for the synthesis of example 6, the title compound was synthesized from [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone (example 42, step 1) and 2-chloropyridine-4-boronic acid. The title compound was obtained in 20% yield as light yellow oil. MS (m/e): 595.1 (MH+, 100%).

Workup

  1. customIn analogy to the procedure described for the synthesis of example 6

Sources & evidence

ORD record
ord-96e7a180dc8e4421bce134f73e5a6610
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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