Water → HCID 11141594, compound

HRID 1297761Notes

Reaction equation

HRID 1297761 reaction equation
[OH:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CC(=O)CC>[CH2:24]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([OH:1])([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]1=[O:11])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-one

Product 1

HCID 11141594HCID 11141594, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Combine 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one (225 mg, 1 mmol) and cesium carbonate (977 mg, 3 mmol) in 2-butanone (5 mL). Add benzyl bromide (0.13 mL, 1 mmol) and heat at 60° C. for 3 h. with vigorous stirring. Dilute the reaction with water and wash with ethyl acetate (2×). Wash combined organic portions with brine and then dry (MgSO4), filter and concentrate in vacuo to give an oil. Purify with radial chromatography (gradient of 10% EtOAc/hexanes to 25% EtOAc/hexanes) to give 204 mg (65%) of the title compound as a white solid. MS (ES): m/z=298 (M+1−H2O); 1H NMR(DMSO-d6); δ7.37-7.27 (m, 11H), 7.18 (m, 1H), 7.05 (m, 1H), 6.98 (m, 1H), 6.87 (s, 1H), 4.92 (s, 2H).

Workup

  1. additionDilute
  2. washwash with ethyl acetate (2×)
  3. washWash
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto give an oil
  8. customPurify with radial chromatography (gradient of 10% EtOAc/hexanes to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-210ba2f979414fd880afdb685df92ca2
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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