Sodium Hydroxide → 5-Bromo-3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine

HRID 908422노트

반응식

HRID 908422 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[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1O.[OH-].[Na+]>O>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:14]3[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 6435622-Amino-6-fluorophenolHCID 7374452-Amino-5-bromonicotinic acid

생성물 1

HCID 673882065-Bromo-3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine수율 33.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
200 °C

실험 절차

A mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (1 g), 2-amino-6-fluoro-phenol (0.586 g) and polyphosphoric acid (10 g) was stirred at 200° C. for 5 hours. The resulting mixture was cooled to room temperature, diluted with water (4 ml) and basified to pH 12 with aqueous NaOH 10N, then 2N. The precipitate was filtered, washed with water, diethyl ether, and dried. The compound was stirred in THF during 2 days, the insoluble was filtered, the filtrate was concentrated to dryness and dried under vacuum to give 5-bromo-3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (0.475 g). NMR Spectrum: (DMSOd6) 7.37-7.48 (m, 2H), 7.69 (dd, 1H), 7.83 (bs, 2H), 8.34 (d, 1H), 8.38 (d, 1H); Mass spectrum: M+H+ 307-309

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with water, diethyl ether
  4. customdried
  5. stirringThe compound was stirred in THF during 2 days
  6. filtrationthe insoluble was filtered
  7. concentrationthe filtrate was concentrated to dryness
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-bd152d22d4b94240b557e3579104edb6
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017611B2

반응 노트

불러오는 중…