Water → HCID 86628337, 화합물

HRID 21338노트

반응식

HRID 21338 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86628337HCID 86628337, 화합물수율 25.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cda688a316bd420eb4294ebce63fa3f3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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