Potassium Phosphate, Tribasic → HCID 59625710, compound

HRID 403293Notes

Reaction equation

HRID 403293 reaction equation
Cl[C:2]1[C:3]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:16]1([C:2]2[C:3]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:4]=3[S:5][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:18][CH2:17]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 762658Methyl 3-chloro-6-fluoro-1-benzothiophene-2-carboxylateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 59625710HCID 59625710, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3-chloro-6-fluorobenzo[b]thiophene-2-carboxylate 12a (150 mg, 0.613 mmol), cyclopropylboronic acid 12b (79 mg, 0.92 mmol), Pd(OAc)2 (20 mg, 0.09 mmol), SPhos (88 mg, 0.215 mmol), and K3PO4 (0.26 g, 1.23 mmol) in toluene (2 mL) was heated to 100° C. for 3 h in a sealed reaction vessel. The reaction was diluted with EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 10% EtOAc/hexanes) to give compound 12c.

Workup

  1. concentrationThe organic layer was concentrated
  2. custompurified by flash column chromatography (silica gel, 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d720c37de40d41fc9be26d1a23d7d5db
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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