Sodium Hydroxide → HCID 67388206, compound

HRID 908422Notes

Reaction equation

HRID 908422 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]=[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

Participants

5

Reactant 3

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

Product 1

HCID 67388206HCID 67388206, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-bd152d22d4b94240b557e3579104edb6
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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