2-Fluorophenylboronic acid → (1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

HRID 630455Notes

Reaction equation

HRID 630455 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]([CH2:25][OH:26])=[CH:9]2)=[N:6][CH:7]=1.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O>>[F: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]([CH2:25][OH:26])=[CH:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 118666263(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 118666239(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

Procedure

Prepared from 27c) (400 mg, 0.959 mmol, 1.0 eq) and (2-fluorophenyl)boronic acid (133 mg, 0.959 mmol, 1.0 eq) according to general procedure 1. White solid. Yield: 230 mg (55% of theory). Melting range: 190-194° C. HPLC (method 1): Rt=9.69 min. Mass spectroscopy: m/z: [M+H]+=433.0

Sources & evidence

ORD record
ord-507d3725e5ad447c99d41e29aa2fb2f1
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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