Potassium Phosphate, Tribasic → HCID 86692516, compound

HRID 1748570Notes

Reaction equation

HRID 1748570 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12](Br)[CH:13]=2)[N:8]([CH3:16])[CH:7]=1)=[O:5])[CH3:2].[CH3:17][C:18]1(C)C(C)(C)OB(C=C)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:17]=[CH2:18])[CH:13]=2)[N:8]([CH3:16])[CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86692444HCID 86692444, compound

Product 1

HCID 86692516HCID 86692516, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-bromo-1-methyl-1H-indole-3-carboxylic acid ethyl ester (1.2 g) described in Reference Example 52 (2) in tetrahydrofuran (14 ml) were added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (983 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (349 mg), palladium acetate (96 mg) and tripotassium phosphate (2.26 g) at room temperature, and stirred at 75° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-methyl-5-vinyl-1H-indole-3-carboxylic acid ethyl ester (934 mg) as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-363bb43c12af4258a073b416dbe32168
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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