Potassium Carbonate → HCID 66657452, compound

HRID 420983Notes

Reaction equation

HRID 420983 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=2)[N:8]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=2)[C:7]=1[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:5])[CH3:2].[F:38][C:39]([F:50])([F:49])[C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>CCOC(C)=O.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>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:43]3[CH:44]=[CH:45][C:40]([C:39]([F:50])([F:49])[F:38])=[CH:41][CH:42]=3)[CH:13]=2)[N:8]([C:23]2[CH:24]=[CH:25][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:27][CH:28]=2)[C:7]=1[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86628821HCID 86628821, compound

Product 1

HCID 66657452HCID 66657452, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture 2-ethoxycarbonylmethyl-1-(4-isopropylphenyl)-5-trifluoromethane-sulfonyloxyindole-3-carboxylic acid ethyl ester (133 mg, 0.25 mmol, see step (a) above), 4-trifluoromethylphenylboronic acid (142 mg, 0.75 mmol), K2CO3 (276 mg, 2 mmol), tetrakis(triphenylphosphine)palladium(0) (78 mg, 0.067 mmol) and anhydrous dioxane (10 mL) was stirred at 90° C. for 4 h. The mixture was diluted with EtOAc (30 mL), washed with saturated NaHCO3 (aq, sat) dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 102 mg (76%).

Workup

  1. washwashed with saturated NaHCO3 (aq, sat)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-0fbb5bf8b04246d5b1f277df5ecace7d
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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