Sodium Carbonate → N-[(7-phenyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

HRID 6236

반응식

HRID 6236 반응식
Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[C:11](=[O:19])[O:12][CH:13]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH:6]3[CH2:5][C:4]=2[CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:20]1([C:2]2[CH:10]=[CH:9][C:8]3[N:7]4[C:11](=[O:19])[O:12][CH:13]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH:6]4[CH2:5][C:4]=3[CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 19795216N-[(7-bromo-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

생성물 1

HCID 54251491N-[(7-phenyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

(±) (1S,9aS/1R,9aR) N-[(7-Bromo-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 24, 129 mg) is dissolved in tetrahydrofuran (1 ml). To this mixture palladium tetrakis(triphenylphosphine) (22 mg), phenylboronic acid (61 mg) and aqueous sodium carbonate (2M, 0.45 ml) is added. The mixture is warmed for 15.5 hours in an oil bath at 68°. The mixture is then partitioned between aqueous sodium carbonate (2M, 2 ml) and methylene chloride (3 ml). After separation of the layers, the aqueous phase is extracted with additional methylene chloride (3×2 ml). The organic layers are combined, dried over magnesium sulfate and concentrated to provide a solid. This solid is taken up in methylene chloride and placed on a 20.5 cm×2.5 cm, 40-63μ silica column and eluted with ethyl acetate/methanol gradient. The appropriate fractions are pooled and concentrated to give the title compound, mp 181°-183°; NMR (CDCl3, 300 MHz) 7.43, 6.08, 4.53, 4.54, 3.83, 3.70, 3.35, 3.17 and 2.07 δ.

후처리

  1. temperatureThe mixture is warmed for 15.5 hours in an oil bath at 68°
  2. customThe mixture is then partitioned between aqueous sodium carbonate (2M, 2 ml) and methylene chloride (3 ml)
  3. customAfter separation of the layers
  4. extractionthe aqueous phase is extracted with additional methylene chloride (3×2 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto provide a solid
  8. washeluted with ethyl acetate/methanol gradient
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0b84c5d8a820414a8eea57ac247ba120
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247090

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