Ethyl Acetate → HCID 25096252, compound

HRID 2425471Notes

Reaction equation

HRID 2425471 reaction equation
[F:1][CH:2]([F:25])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([OH:24])[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[CH3:6].Br[C:27]1[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[N:31][CH:32]=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>[F:25][CH:2]([F:1])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([O:24][C:27]2[CH:32]=[N:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[CH3:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 134334245-Bromo-2-methanesulfonylpyridineHCID 59205104HCID 59205104, compound

Product 1

HCID 25096252HCID 25096252, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-N-(5-methylpyrazin-2-yl)benzamide (190 mg, 0.54 mmol), 5-bromo-2-methylsulfonyl-pyridine (CAS no. 98626-95-0) (140 mg, 0.59 mmol), cesium carbonate (350 mg, 1.08 mmol) and bromotris(triphenylphosphine)copper(I) (101 mg, 0.11 mmol) in DMA (5 mL) was stirred in a microwave reactor at 160° C. for 6 hours. Ethyl acetate (50 mL) was added and the mixture washed with water (50 mL), brine (50 mL), dried (MgSO4) and reduced in vacuo. The crude residue was chromatographed on silica, eluting with 10-100% ethyl acetate in isohexane, to give the desired compound (19 mg).

Workup

  1. washthe mixture washed with water (50 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. customThe crude residue was chromatographed on silica
  4. washeluting with 10-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-f9b2e16ad0d84863ac30cccecbc87335
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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