Potassium Carbonate → HCID 118598196, compound

HRID 63620Notes

Reaction equation

HRID 63620 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]3[C:6](=[O:12])[CH2:7][CH2:8][O:9][C:10]=3[CH:11]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 118598196HCID 118598196, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 7-bromo-4-chromanone (1.0 g, 4.4 mmol) in DMF (15 mL) was added [4-(trifluoromethyl)phenyl]boronic acid (1.25 g, 6.6 mmol), Pd(PPh3)4 (580 mg, 0.5 mmol) and K2CO3 (1.22 g, 8.8 mmol). The mixture was stirred at 105° C. for 4 h under nitrogen. The mixture was filtered and concentrated, and the residue was purified by silica gel chromatography (PE:EtOAc=4:1) to give 830 mg (61%) of the title compound as white solid. [M+H] Calc'd for C16H11F3O2, 293. Found, 293.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by silica gel chromatography (PE:EtOAc=4:1)

Sources & evidence

ORD record
ord-4a217c1b064e4c79a4021a3e06b28218
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

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