4-Cyanophenylboronic acid → 4-[5-(1-Isopropyl-piperidin-4-yloxy)-2-(morpholine-4-carbonyl)-indol-1-yl]-benzonitrile

HRID 19871Notes

Reaction equation

HRID 19871 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]([C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:21])=[CH:14]3)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)#[N:29]>>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:33]2[CH:34]=[CH:35][C:30]([C:28]#[N:29])=[CH:31][CH:32]=2)[C:15]([C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:21])=[CH:14]3)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 11717680(5-(1-isopropylpiperidin-4-yloxy)-1H-indol-2-yl)(morpholino)methanone2×

Product 1

HCID 167395914-[5-(1-Isopropyl-piperidin-4-yloxy)-2-(morpholine-4-carbonyl)-indol-1-yl]-benzonitrile

Procedure

In analogy to the procedure described for the synthesis of example 6, the title compound was synthesized from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone (intermediate 2) and 4-cyanophenylboronic acid. The title compound was obtained in 31% yield as yellow foam. MS (m/e): 473.2 (MH+, 100%).

Workup

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

Sources & evidence

ORD record
ord-80ac577fc94c432c9e5c0805a6d801e4
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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