Water → HCID 59442699, compound

HRID 657509Notes

Reaction equation

HRID 657509 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH2:13][CH2:12][C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.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.CC(=O)OCC>[CH:25]1([CH2:24][O:23][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([C:32]4[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=4)=[CH:7][CH:6]=3)[CH2:9][CH2:10][C:11]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)[CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 684800454-(4-Bromophenyl)-4-cyclopropylmethoxy-1-phenylcyclohexanecarboxylic acid

Product 1

HCID 59442699HCID 59442699, compoundYield 9.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

19 mg of tetrakis(triphenylphosphine)palladium(0) were added to a solution of 200 mg of 4-(4-bromophenyl)-4-cyclopropylmethoxy-1-phenylcyclohexanecarboxylic acid in 4 ml of degassed toluene under argon in a two-necked flask and the mixture was stirred for 10 min at room temperature. Subsequently, 65.1 mg of 4-fluorobenzeneboronic acid and 0.341 ml of a 2 M sodium carbonate solution were added and the reaction mixture was heated for 24 h at 100° C. After cooling, water and EA were added, the organic phase was separated and the aqueous phase was extracted twice with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. After purification of the residue by preparative HPLC, 20 mg of the title compound were obtained as a white lyophilizate.

Workup

  1. temperaturethe reaction mixture was heated for 24 h at 100° C
  2. temperatureAfter cooling
  3. customthe organic phase was separated
  4. extractionthe aqueous phase was extracted twice with EA
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customAfter purification of the residue by preparative HPLC

Sources & evidence

ORD record
ord-31b87729e7b34da9801d2e23f51144ad
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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