Dimethylformamide → (2,4-Difluoro-3-formyl-phenyl)-carbamic acid tert-butyl ester

HRID 250675노트

반응식

HRID 250675 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:32]=[O:33]>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH:32]=[O:33])[C:9]=1[F:15])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 22986665Tert-butyl (2,4-difluorophenyl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 58086596(2,4-Difluoro-3-formyl-phenyl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 2,4-difluoro-phenyl)-carbamic acid tert-butyl ester (123, 1.41 g, 6.17 mmol) in tetrahydrofuran (60.0 mL) under an atmosphere of nitrogen at 78° C. were added n-butyllithium (2.50 M in hexane, 2.59 mL) for 30 min. Lithium diisopropylamide (2.0 M in hexane, 3.4 mL) was added to the reaction. After 35 min, N,N-dimethylformamide (1.05 mL, 0.0136 mol) was added to the reaction mixture. The reaction was allowed to cool to room temperature overnight. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography, eluting with 20% ethyl acetate in hexane to provide compound 124.

후처리

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-b5f51c308a444db3be8f59b8a066e16b
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863288B2

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