Potassium Carbonate → HCID 59619234, compound

HRID 1367566Notes

Reaction equation

HRID 1367566 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@H:9]2[CH2:13][C@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](Br)=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:11][C@@H:10]2[O:28][CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:3]1([NH:6][C:7]([C@H:9]2[CH2:13][C@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:24]([F:27])([F:25])[F:26])(=[O:16])=[O:15])[CH2:11][C@@H:10]2[O:28][CH:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 59619292HCID 59619292, compound

Product 1

HCID 59619234HCID 59619234, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Argon was bubbled through a mixture of (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-(tetrahydro-pyran-4-yloxy)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (40 mg, 0.0707 mmol, example 169) and K2CO3 (20 mg, 0.1415 mmol) in n-butanol (2 ml) for 10 minutes. Then triphenyl-phosphine (1.48 mg, 0.00566 mmol) and palladium acetate (0.318 mg, 0.001415 mmol) were added and the reaction mixture was stirred at 100° C. for 2 h. The mixture was allowed to cool to room temperature, the solvent was removed and the remaining residue was diluted with water and extracted 3 times with EtOAc. The combined extracts were washed with brine, dried (Na2SO4) and evaporated. The remaining residue was purified by silica column chromatography (DCM/MeOH 98:2) to obtain the title compound contaminated with a small amount of triphenyl-phosphine oxide. This material was triturated with a small amount of ether to give the title compound (25 mg, 73%) as white solid. MS (EI): 487.3 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed
  3. additionthe remaining residue was diluted with water
  4. extractionextracted 3 times with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe remaining residue was purified by silica column chromatography (DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-fa98838c96ee4d7c9c24315b17891163
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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