Water → HCID 21921136, compound

HRID 1695576Notes

Reaction equation

HRID 1695576 reaction equation
Br[C:2]1([F:20])[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[O:7])=[CH:4][CH2:3]1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].O>COCCOC>[F:20][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([C:22]([F:33])([F:32])[F:21])[CH:28]=3)[CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 17749109Barium hydroxide, octahydrateHCID 67270459HCID 67270459, compound

Product 1

HCID 21921136HCID 21921136, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

150 mg (0.45 mmoles) 4-bromo-N-indan-2-yl-4-fluoro-benzamide, 102 mg (0.54 mmoles) 3-trifluoromethylbenzeneboronic acid, 211 mg (0.67 mmoles) barium hydroxide octahydrate and 20 mg tetrakis-triphenylphosphine-palladium were suspended in 10 ml 1,2-dimethoxyethane and 10 ml water and heated to reflux for 7 h. Subsequently, the reaction mixture was evaporated to dryness, the residue taken up in methylenchloride and extracted twice with water. The oil remaining after evaporation of the organic phase was purified using prep. HPLC chromatography. (RP18, acetonitrile/water, 1% trifluoroacetic acid). 80 mg (45%) of the title compound were obtained.

Workup

  1. temperatureto reflux for 7 h
  2. customSubsequently, the reaction mixture was evaporated to dryness
  3. extractionextracted twice with water
  4. customafter evaporation of the organic phase
  5. customwas purified

Sources & evidence

ORD record
ord-f125d8644fd547bbb0b70960482d8049
Source dataset
uspto-grants-2012_04
Patent number
US08163751B2

Reaction notes

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