Hydrochloric Acid → HCID 67270138, compound

HRID 1695575Notes

Reaction equation

HRID 1695575 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]1[CH:29]=[CH:28][C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=1.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[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[CH:27]=[CH:26][C:25]3[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=3)[CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 678834-FluorostyreneHCID 67270459HCID 67270459, compound

Product 1

HCID 67270138HCID 67270138, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

150 mg (0.45 mmoles) 4-bromo-N-indan-2-yl-4-fluoro-benzamide, 1 mg palladium-(II)-acetate, 3.4 mg tri-o-tolyl phosphine and 88 mg (0.72 mmoles) para-fluorostyrene were combined in 2 ml triethylamine and stirred under reflux for 9 h. Subsequently, the reaction mixture was poured on a mixture of ice and diluted HCl, the mixture extracted with ethyl acetate and the resulting solution dried and evaporated to dryness. The residual oil was purified using prep. HPLC chromatography. (RP18, acetonitrile/water, 1% trifluoroacetic acid). 152 mg (90%) 4-fluoro-N-{4-[2-(4-fluoro-phenyl)-vinyl]-indan-2-yl}-benzamide were obtained.

Workup

  1. temperatureunder reflux for 9 h
  2. extractionthe mixture extracted with ethyl acetate
  3. customthe resulting solution dried
  4. customevaporated to dryness
  5. customThe residual oil was purified

Sources & evidence

ORD record
ord-da8f060732b04bf8a563661cba611ca9
Source dataset
uspto-grants-2012_04
Patent number
US08163751B2

Reaction notes

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