Dimethylformamide → Tert-butyl 4-(2-fluoro-3-formylbenzoyl)piperazine-1-carboxylate

HRID 1725508노트

반응식

HRID 1725508 반응식
Br[C:2]1[C:3]([F:23])=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:6].C([Mg]Cl)C(C)C.CN(C)[CH:32]=[O:33].[Cl-].[NH4+]>O1CCCC1>[F:23][C:3]1[C:2]([CH:32]=[O:33])=[CH:22][CH:21]=[CH:20][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:6]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57562603Tert-butyl 4-(3-bromo-2-fluorobenzoyl)piperazine-1-carboxylateHCID 178418368HCID 178418368, 화합물

생성물 1

HCID 57562639Tert-butyl 4-(2-fluoro-3-formylbenzoyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

194 mg of tert-butyl 4-(3-bromo-2-fluorobenzoyl)piperazine-1-carboxylate was dissolved in 5.0 ml of tetrahydrofuran, and 1.25 ml of a solution of isobutylmagnesium chloride in tetrahydrofuran (2.0 M) was added thereto at −78° C. After stirring at the same temperature for 2 hours, 0.39 ml (5.0 mmol) of N,N-dimethylformamide was added thereto. The resulting mixture was stirred at the same temperature for 30 minutes and further stirred at 0° C. for 30 minutes. To the reaction mixture was added saturated ammonium chloride, and the mixture was extracted with chloroform. The organic layer was washed with brine and then concentrated. The residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 1/1) to give the title compound.

후처리

  1. customat −78° C
  2. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  3. stirringfurther stirred at 0° C. for 30 minutes
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated
  7. customThe residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 1/1)

출처 및 근거

ORD 기록
ord-38054f819b814ab2a2456e7d7eec6692
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491720B2

반응 노트

불러오는 중…