2-Chlorophenylboronic acid → (1-(5-(2-Chlorophenyl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

HRID 630444Notes

Reaction equation

HRID 630444 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])[CH:15]=3)[C:10]([S:25][CH3:26])=[CH:9]2)=[N:6][CH:7]=1.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O>>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])[CH:15]=3)[C:10]([S:25][CH3:26])=[CH:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 118666053(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 118666113(1-(5-(2-Chlorophenyl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Procedure

Synthesized according to general procedure 1 from (1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone (1.0 g, 2.30 mmol, 1.0 eq) and (2-chlorophenyl)boronic acid (0.429 g, 2.77 mmol, 1.2 eq). Yield: 0.7 g (65% of theory).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-34dcaef13bea4fa9afc9a41bbb370f2e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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