Trifluoroacetic acid → 6-Bromo-5-fluoropyridin-2-amine

HRID 1396478

반응식

HRID 1396478 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:15][C:10]1[N:9]=[C:8]([NH2:7])[CH:13]=[CH:12][C:11]=1[F:14]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71744124Tert-butyl (6-bromo-5-fluoropyridin-2-YL)carbamate

생성물 1

HCID 596058336-Bromo-5-fluoropyridin-2-amine수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (6-bromo-5-fluoro-pyridin-2-yl)-carbamic acid tert-butyl ester (1.43 g, 4.91 mmol) in DCM (25 mL) was added TFA (3.78 mL, 49.1 mmol, Eq: 10.0). The mixture was stirred at room temperature for 2 h, after which it was concentrated in vacuo, and redissolved in EtOAc. The organic layer was washed with sat. aq. NaHCO3 followed by water and brine. The resulting organic layer was concentrated on to silica gel and chromatographed (10% to 40% EtOAc/hexanes) to give 6-bromo-5-fluoro-pyridin-2-ylamine (850 mg, 91%). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.23 (dd, J=8.6, 7.5 Hz, 1H), 6.41 (dd, J=8.6, 2.6 Hz, 1H), 4.40 (br. s, 2H).

후처리

  1. concentrationafter which it was concentrated in vacuo
  2. dissolutionredissolved in EtOAc
  3. washThe organic layer was washed with sat. aq. NaHCO3
  4. concentrationThe resulting organic layer was concentrated on to silica gel
  5. customchromatographed (10% to 40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-cc36f01cdd014233bd45c2777bbfdcf9
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901124B2

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