2-Amino-5-bromonicotinic acid → 5-Bromo-3-(6,7-difluoro-1,3-benzoxazol-2-yl)pyridin-2-amine

HRID 908420노트

반응식

HRID 908420 반응식
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[NH2:12][C:13]1[C:18](O)=[C:17]([F:20])[C:16]([F:21])=[CH:15][CH:14]=1>O.[OH-].[Na+].ClCCl>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:18]3[C:17]([F:20])=[C:16]([F:21])[CH:15]=[CH:14][C:13]=3[N:12]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

참가 물질

6

반응물 2

HCID 7374452-Amino-5-bromonicotinic acidHCID 27784416-Amino-2,3-difluorophenol

생성물 1

HCID 673886015-Bromo-3-(6,7-difluoro-1,3-benzoxazol-2-yl)pyridin-2-amine수율 22.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
200 °C

실험 절차

To a mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (1 g) and 6-amino-2,3-difluoro-phenol (0.669 g) placed in a round bottom flask was added polyphosphoric acid (10 g). The mixture was heated at 200° C. for 5 hours. A homogenous black mixture was obtained. The mixture was diluted in water and neutralizing to pH 8 with NaOH 2N. The heterogeneous mixture was diluted with dichloromethane. The insoluble was filtered. The organic phase was separated. The aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with brine, dried on sodium sulfate, evaporated and dried to afford 5-bromo-3-(6,7-difluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (0.338 g). NMR Spectrum: (DMSOd6) 7.54 (ddd, 1H), 7.70 (ddd, 1H), 7.79 (bs, 2H), 8.34 (d, 1H), 8.38 (d, 1H); Mass spectrum: M+H+ 326-328

후처리

  1. customplaced in a round bottom flask
  2. customA homogenous black mixture was obtained
  3. filtrationThe insoluble was filtered
  4. customThe organic phase was separated
  5. extractionThe aqueous phase was extracted twice with dichloromethane
  6. washThe combined organic phases were washed with brine
  7. customdried on sodium sulfate
  8. customevaporated
  9. customdried

출처 및 근거

ORD 기록
ord-156fbbb8476e4b2f975d8763b37f2b69
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017611B2

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