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

HRID 908420ノート

反応式

HRID 908420 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[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
200 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-156fbbb8476e4b2f975d8763b37f2b69
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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