Water → HCID 22042613, compound

HRID 1791016Notes

Reaction equation

HRID 1791016 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].O.[OH:19][C:20]([C:27]1[CH:32]=[CH:31][C:30]([N:33]([CH2:43][CH:44]([CH3:46])[CH3:45])[S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])=[CH:29][CH:28]=1)([C:23]([F:26])([F:25])[F:24])[C:21]#[CH:22]>[Pd].COCCOC.[Cu]I>[OH:19][C:20]([C:27]1[CH:32]=[CH:31][C:30]([N:33]([CH2:43][CH:44]([CH3:46])[CH3:45])[S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])=[CH:29][CH:28]=1)([C:23]([F:26])([F:25])[F:24])[C:21]#[C:22][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][CH:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 22042620HCID 22042620, compound

Product 1

HCID 22042613HCID 22042613, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

80.6 mg (0.39 mmol) 2-Bromonaphthalene, 21 mg palladium on carbon (10% Pd), 74.1 mg (0.39 mmol) copper (I) iodide, and 135 mg (0.98 mmol) K2CO3 were combined 2 mL of DME and 2 mL of water and the resulting mixture was stirred at room temperature for 30 min. A solution of 80 mg (0.2 mmol) of N-[4-(1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-N-isobutyl-benzenesulfonamide (Example 75) in 1 mL of DME was added and the reaction mixture was stirred at 65° C. overnight. The catalyst was removed by filtration over a pad of celite. The filtrate was washed with a saturated aqueous solution of ammonium chloride and brine. The organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc=9:1) to give the title compound.

Workup

  1. stirringthe reaction mixture was stirred at 65° C. overnight
  2. customThe catalyst was removed by filtration over a pad of celite
  3. washThe filtrate was washed with a saturated aqueous solution of ammonium chloride and brine
  4. dry with materialThe organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc=9:1)

Sources & evidence

ORD record
ord-4b6978f8aa5c4493b9190309ea64498e
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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