5-Cyano-2-fluorobenzeneboronic acid → 4-Fluoro-3-(2-(3-(methylthio)-6-(morpholine-4-carbonyl)-1H-indol-1-yl)pyrimidin-5-yl)benzonitrile

HRID 630443Notes

Reaction equation

HRID 630443 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.[C:27]([C:29]1[CH:30]=[CH:31][C:32]([F:38])=[C:33](B(O)O)[CH:34]=1)#[N:28]>>[F:38][C:32]1[CH:33]=[CH:34][C:29]([C:27]#[N:28])=[CH:30][C:31]=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 27833615-Cyano-2-fluorobenzeneboronic acidHCID 118666053(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 1186663504-Fluoro-3-(2-(3-(methylthio)-6-(morpholine-4-carbonyl)-1H-indol-1-yl)pyrimidin-5-yl)benzonitrile

Procedure

Synthesized according to general procedure 1 from (1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone (1.0 g, 2.309 mmol, 1.0 eq) and (5-cyano-2-fluorophenyl)boronic acid (0.451 g, 2.77 mmol, 1.2 eq). Yield: 0.4 g (36% of theory)

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-22a11d174023497a98f68ab5fc9a9873
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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