Water → HCID 86628337、化合物

HRID 21338ノート

反応式

HRID 21338 の反応式
[Br:1][C:2]1[N:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5].[Li+].CC([N-]C(C)C)C.CCCCCCC.C1C[O:38][CH2:37]C1.C(C1C=CC=CC=1)C.CN(C=O)C.O>C1COCC1>[Br:1][C:2]1[C:3]2[C:4](=[O:5])[N:6]([C:7]([CH3:15])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:8])[CH:37]([OH:38])[C:16]=2[CH:17]=[CH:18][N:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 86590273LDA THF ethylbenzene heptaneHCID 866283362-bromo-N-(1-methyl-1-phenylethyl)nicotinamide

生成物 1

HCID 86628337HCID 86628337、化合物収率 25.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Bromo-N-(1-methyl-1-phenylethyl)nicotinamide (500 mg, 1.57 mmol) was dissolved in THF (20 mL), and the solution was added with LDA-heptane/THF/ethylbenzene solution (2.0 mol/L, 3.5 mL, 7.1 mmol) by drops at −78° C. for 25 minutes under argon atmosphere, followed by stirring at the same temperature for 1.6 hours. Then, the mixture was added with DMF (0.267 mL, 3.45 mmol) and warmed from −78° C. to room temperature over 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/1 to 97/3) to obtain 4-bromo-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (138 mg, yield 25%).

後処理

  1. temperaturewarmed from −78° C. to room temperature over 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash column chromatography (chloroform/methanol=100/1 to 97/3)

出典と根拠

ORDレコード
ord-cda688a316bd420eb4294ebce63fa3f3
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

反応ノート

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