Dimethylformamide → N-(2-Fluoro-6-formylphenyl)pivalamide

HRID 1172360노트

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HRID 1172360 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].C([Li])CCC.C1CCCCC1.CN(C)[CH:29]=[O:30]>O1CCCC1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:29]=[O:30])[C:3]=1[NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8078CyclohexaneHCID 44203089N-(2-Bromo-6-fluorophenyl)pivalamideHCID 178418339Butyllithium

생성물 1

HCID 59424313N-(2-Fluoro-6-formylphenyl)pivalamide수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

N-(2-Bromo-6-fluorophenyl)pivalamide (25.5 mmol, 7.0 g) was dissolved in tetrahydrofuran (200 mL). Mixture was cooled to −78° C. 2M Butyllithium in cyclohexane (62.0 mmol, 31.0 mL) was added to the mixture drop-wise. Reaction mixture was held at −78° C. for 30 minutes. A solution of N,N-dimethylformamide (129 mmol, 10.0 mL) in tetrahydrofuran (30 mL) was added to the reaction mixture drop-wise. Reaction was held at −78° C. for 30 minutes. Reaction was quenched with aqueous ammonium chloride then the mixture was allowed to warm to room temperature. Mixture was extracted 2× ethyl acetate. Combined organic layers were dried (magnesium sulfate), filtered and concentrated. Silica gel chromatography afforded the desired product as white solid in 80% yield. 1H NMR (300 MHz, CDCl3): δ=9.93 (d, J=1.83, 1H), 9.14 (bs, 1H), 7.56-7.50 (m, 1H), 7.42-7.25 (m, 2H), 1.34 (s, 9H). MS m/e (M+H)+=224.2.

후처리

  1. customReaction mixture
  2. customReaction
  3. waitwas held at −78° C. for 30 minutes
  4. customReaction
  5. customwas quenched with aqueous ammonium chloride
  6. temperatureto warm to room temperature
  7. extractionMixture was extracted 2× ethyl acetate
  8. dry with materialCombined organic layers were dried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-acaf17d204424d70bb9b6c28706d036b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834007B2

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