3-Cyano-4-fluorophenylboronic acid → 5-[2-(4,4-Difluoro-piperidine-1-carbonyl)-5-(1-isopropyl-piperidin-4-yloxy)-indol-1-yl]-2-fluoro-benzonitrile

HRID 19872Notes

Reaction equation

HRID 19872 reaction equation
[F:1][C:2]1([F:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[C:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[F:38])#[N:31]>>[F:29][C:2]1([F:1])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[N:11]([C:34]3[CH:35]=[CH:36][C:37]([F:38])=[C:32]([CH:33]=3)[C:30]#[N:31])[C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:27])[CH3:28])[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 27579643-Cyano-4-fluorophenylboronic acidHCID 11603838(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanone2×

Product 1

HCID 167395925-[2-(4,4-Difluoro-piperidine-1-carbonyl)-5-(1-isopropyl-piperidin-4-yloxy)-indol-1-yl]-2-fluoro-benzonitrile

Procedure

In analogy to the procedure described for the synthesis of example 6, the title compound was synthesized from (4,4-difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone (intermediate 1) and 3-cyano-4-fluorophenylboronic acid. The title compound was obtained in 22% yield as orange oil. MS (m/e): 525.2 (MH+, 100%).

Workup

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

Sources & evidence

ORD record
ord-1dd9a7d41a284fd4948d82969b4b5de7
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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