Potassium Phosphate, Tribasic → HCID 58486802, compound

HRID 874676Notes

Reaction equation

HRID 874676 reaction equation
Br[C:2]1[C:3]2[CH2:11][CH2:10][CH2:9][CH2:8][C:4]=2[S:5][C:6]=1[CH3:7].FC1(F)OC2C=C(C)C(C3N=C[C:25]([NH:28][C:29](=O)[C:30]4[CH:35]=[CH:34]C=CC=4F)=[N:26]C=3)=CC=2O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(#N)C.O>[CH3:7][C:6]1[S:5][C:4]2[CH2:8][CH2:9][CH2:10][CH2:11][C:3]=2[C:2]=1[C:30]1[CH:35]=[CH:34][C:25]([NH2:26])=[N:28][CH:29]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamideHCID 584872903-Bromo-2-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene

Product 1

HCID 58486802HCID 58486802, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 67448433Dioxane acetonitrile waterSolvent

Conditions

Temperature
90 °C

Procedure

Palladium tetrakis-triphenylphosphine (12 mg, 10 μmol) was added to a degassed solution of bromide 239 (46 mg, 0.2 mmol) and boronate 11 (88 mg, 0.4 mmol) in dioxane:acetonitrile:water (9:9:2, 1.5 mL) and potassium phosphate (63 mg, 0.3 mmol). The resulting mixture was heated under argon at 90° C. with stirring for 4 hours. The mixture was then cooled, extracted with dichloromethane (3×10 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 240 (32 mg, 66%) as an oil: LRESIMS m/z 245.1 [M+H]+, calcd. for C14H17N2S1 245.1.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with dichloromethane (3×10 mL)
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f9288ea63434020aa44818199dc662e
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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