Tolylboronic acid → [5-(1-Isopropyl-piperidin-4-yloxy)-1-p-tolyl-1H-indol-2-yl]-morpholin-4-yl-methanone

HRID 19869

Reaction equation

HRID 19869 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].[CH3:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[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:32]2[CH:33]=[CH:34][C:29]([CH3:28])=[CH:30][CH:31]=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 79799Tolylboronic acidHCID 11717680(5-(1-isopropylpiperidin-4-yloxy)-1H-indol-2-yl)(morpholino)methanone2×

Product 1

HCID 16739561[5-(1-Isopropyl-piperidin-4-yloxy)-1-p-tolyl-1H-indol-2-yl]-morpholin-4-yl-methanone

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-methylbenzeneboronic acid. The title compound was obtained in 57% yield as a yellow foam. MS (m/e): 462.2 (MH+, 100%).

Workup

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

Sources & evidence

ORD record
ord-2e61059cfd6d4154b127a196e0f3dd59
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Linked notes

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