Ethyl Acetate → HCID 59205089, compound

HRID 2425493Notes

Reaction equation

HRID 2425493 reaction equation
[F:1][CH:2]([F:19])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:11]([O:13]C)=[O:12])[CH3:6].Br[C:21]1[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[N:25][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CC(N(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Br.O>[F:1][CH:2]([F:19])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][C:21]2[CH:26]=[N:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH:17]=1)[C:11]([OH:13])=[O:12])[CH3:6]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 134334245-Bromo-2-methanesulfonylpyridineHCID 59127138methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-benzoate

Product 1

HCID 59205089HCID 59205089, compound

Reagents, catalysts & solvents 3

HCID 11251615Bromotris(triphenylphosphine)copper(I)CatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-benzoate (233 mg, 0.84 mmol), 5-bromo-2-methylsulfonyl-pyridine (CAS no. 98626-95-0) (200 mg, 0.84 mmol), cesium carbonate (549 mg, 1.69 mmol) and bromotris(triphenylphosphine)copper(I) (157 mg, 0.17 mmol) in DMA (5 mL) was stirred in a microwave reactor at 160° C. for 6 hours. Ethyl acetate (50 mL) and water were added and the aqueous layer was acidified and extracted with ethyl acetate (2×50 mL). The combined organics were washed with brine, dried (MgSO4) and reduced in vacuo to give the desired compound (0.16 g).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-a0dbd6a9fe0c4c52a9844618f0f9557e
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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