Dimethylformamide → tert-butyl N-(4-fluoro-3-formylpyridin-2-yl)carbamate

HRID 920124

반응식

HRID 920124 반응식
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[Li]CCCC.CN([CH:24]=[O:25])C>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[C:3]=1[CH:24]=[O:25]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 51354888tert-butyl N-(4-fluoropyridin-2-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 89670239tert-butyl N-(4-fluoro-3-formylpyridin-2-yl)carbamate수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of tert-butyl 4-fluoropyridin-2-ylcarbamate (1 g, 4.72 mmol) in THF (20 mL) was added dropwise n-BuLi (4.7 mL, 11.8 mmol) at −78° C. After stirring for 0.5 h, a solution of DMF (2 mL) in THF (2 mL) was added dropwise at −78° C. TLC indicated the reaction was completed. The reaction was quenched with 1N HCl at −78° C. to pH=4. Then water (20 mL) was added and extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc:PE=1:2) to give the title compound (0.65 g, 57%) as a white solid. 1H-NMR (600 MHz, DMSO-d6) δ 10.35 (s, 1H), 9.99 (s, 1H), 8.58-8.56 (m, 1H), 7.23-7.21 (m, 1H), 1.46 (s, 9H) ppm.

후처리

  1. customThe reaction was quenched with 1N HCl at −78° C. to pH=4
  2. additionThen water (20 mL) was added
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (EtOAc:PE=1:2)

출처 및 근거

ORD 기록
ord-076440773d67442988b85b120393a049
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273046B2

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