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

HRID 1396478ノート

反応式

HRID 1396478 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 596058336-Bromo-5-fluoropyridin-2-amine収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cc36f01cdd014233bd45c2777bbfdcf9
出典データセット
uspto-grants-2014_12
特許番号
US08901124B2

反応ノート

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