Pivaloyl chloride → 6-Fluoro-2-pivaloylaminopyridine

HRID 132370노트

반응식

HRID 132370 반응식
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12]>N1C=CC=CC=1>[F:1][C:2]1[N:7]=[C:6]([NH:8][C:11](=[O:12])[C:10]([CH3:15])([CH3:14])[CH3:9])[CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 62493Pivaloyl chlorideHCID 27613996-Fluoropyridin-2-amine

생성물 1

HCID 131542516-Fluoro-2-pivaloylaminopyridine수율 93.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

6-fluoropyridin-2-amine (13.1 g, 117 mmol) was dissolved in anhydrous pyridine (100 mL), and cooled to 0° C. followed by fast dropwise addition of trimethylacetyl chloride (15.9 mL, 129 mmol) over 2 min. 5 min later, the resulting slurry was stirred over night at room temperature. Partial of the solvent was removed on rotary vacuum. The residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL). After separation, the organic layer was washed with brine (50 mL), dried over MgSO4, concentrated on rotary vacuum, and purified on flash chromatography eluting with 25˜75% EtOAc/Hexanes (1400 mL) to afford the expected product as a white solid (21.4 g, 93% yield); 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 9 H), 6.63 (dd, J=8.06, 2.01 Hz, 1 H), 7.76 (q, J=8.14 Hz, 1 H), 7.85 (s, 1 H), 8.09 (dd, J=8.06, 1.76 Hz, 1 H); Mass spec. 197.15 (MH+), Calc. for C10H13FN2O196.1.

후처리

  1. customPartial of the solvent was removed on rotary vacuum
  2. customThe residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL)
  3. customAfter separation
  4. washthe organic layer was washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated on rotary vacuum
  7. custompurified on flash chromatography
  8. washeluting with 25˜75% EtOAc/Hexanes (1400 mL)

출처 및 근거

ORD 기록
ord-65fc9951c02545a7b71c682e48a2dac4
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

반응 노트

불러오는 중…