Ethyl Acetate → HCID 25096254, compound

HRID 2425497Notes

Reaction equation

HRID 2425497 reaction equation
[F:1][CH:2]([F:24])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([OH:23])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12])[CH3:6].Br[C:26]1[CH:27]=[CH:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[N:30][CH:31]=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:24][CH:2]([F:1])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C:26]2[CH:31]=[N:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12])[CH3:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 134334245-Bromo-2-methanesulfonylpyridineHCID 591271223-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-N-(1-methylpyrazol-3-yl)benzamide

Product 1

HCID 25096254HCID 25096254, 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-(1-methylpyrazol-3-yl)benzamide (100 mg, 0.29 mmol), 5-bromo-2-methylsulfonyl-pyridine (CAS no. 98626-95-0) (77 mg, 0.32 mmol), cesium carbonate (191 mg, 0.59 mmol) and bromotris(triphenylphosphine)copper(I) (55 mg, 0.06 mmol) in DMA (5 mL) was stirred in a microwave reactor at 160° C. for 6 hours. Ethyl acetate (50 mL) was added and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and reduced in vacuo. The residue was chromatographed on silica, eluting with 10-80% ethyl acetate in isohexane to give the desired compound (31 mg).

Workup

  1. washwashed with water (50 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on silica
  5. washeluting with 10-80% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-de1175b66f5348b4876dfd59540f2479
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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