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

HRID 6236

反応式

HRID 6236 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(±) (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.

後処理

  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

出典と根拠

ORDレコード
ord-0b84c5d8a820414a8eea57ac247ba120
出典データセット
uspto-grants-1993_09
特許番号
US05247090

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