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

HRID 908422ノート

反応式

HRID 908422 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
200 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-bd152d22d4b94240b557e3579104edb6
出典データセット
uspto-grants-2011_09
特許番号
US08017611B2

反応ノート

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