Potassium Fluoride → (1-(5-(2,3-Difluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)-methanone

HRID 630461Notes

Reaction equation

[F-].[K+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O.Br[C:15]1[CH:16]=[N:17][C:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[O:31])[CH:28]=3)[C:23]([S:38]([CH3:40])=[O:39])=[CH:22]2)=[N:19][CH:20]=1>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C:15]1[CH:20]=[N:19][C:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[O:31])[CH:28]=3)[C:23]([S:38]([CH3:40])=[O:39])=[CH:22]2)=[N:17][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium fluoride (0.048 g, 0.83 mmol), 2,3-difluoro phenyl boronic acid (0.10 g, 0.67 mmol), and bis(tri-tert-butylphosphine)palladium(0) (0.026 g, 0.05 mmol) were added at room temperature under an argon atmosphere to a solution of [1-(5-bromo-pyrimidin-2-yl)-3-methanesulfinyl-1H-indol-6-yl]-morpholin-4-yl-methanone (0.15 g, 0.33 mmol) in dry THF (12 mL). The reaction mixture was heated at 70° C. for 16 h, then filtered through a plug of celite and concentrated. The residue was purified by flash column chromatography [methanol/dichloromethane=1:40]. White solid. Yield: 100 mg (63% of theory).

Workup

filtrationfiltered through a plug of celite
concentrationconcentrated
customThe residue was purified by flash column chromatography [methanol/dichloromethane=1:40]

Sources & evidence

ORD record: ord-85922bac02304f4eb20e021b65190eca
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315490B2

Reaction notes

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