Sodium Hydroxide → HCID 67388485, compound

HRID 908421Notes

Reaction equation

HRID 908421 reaction equation
[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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1O.[OH-].[Na+]>O>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:14]3[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=3[N:12]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 7374452-Amino-5-bromonicotinic acidHCID 27359172-Amino-4-fluorophenol

Product 1

HCID 67388485HCID 67388485, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (1 g) and 2-amino-4-fluoro-phenol (0.586 g) placed in a round bottom flask was added polyphosphoric acid (10 g). The mixture was heated at 200° C. for 16 hours. After cooling, water (75 ml) was added and the mixture was stirred for 30 min. The mixture was basified to pH 12 with concentrated sodium hydroxide solution (6N and 2N). The solid was filtered, washed with water (150 ml×2), and ether (50 ml×2) to afford 5-bromo-3-(5-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (1.0 g). NMR Spectrum: (DMSOd6) 7.53 (ddd, 1H), 7.93 (dd, 1H), 7.99-8.06 (m, 3H), 8.52 (d, 1H), 8.56 (d, 1H); Mass spectrum: M+H+ 308-310

Workup

  1. customplaced in a round bottom flask
  2. temperatureAfter cooling
  3. filtrationThe solid was filtered
  4. washwashed with water (150 ml×2), and ether (50 ml×2)

Sources & evidence

ORD record
ord-a4a49409679840f1b9bcc805688d0d1d
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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