Sodium Hydroxide → HCID 67388662, compound

HRID 908423Notes

Reaction equation

HRID 908423 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[C:18](O)=[CH:17][CH:16]=[C:15]([CH3:20])[N:14]=1.[OH-].[Na+]>O>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:18]3[C:13]([N:12]=2)=[N:14][C:15]([CH3:20])=[CH:16][CH:17]=3)[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 885002-Amino-6-methylpyridin-3-olHCID 7374452-Amino-5-bromonicotinic acid

Product 1

HCID 67388662HCID 67388662, compoundYield 35.6%

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-methyl-pyridin-3-ol (1.4 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 reaction mixture was extracted with dichloromethane/acetonitrile, the organic phase was washed with water, a saturated aqueous solution of brine, dried over magnesium sulfate and concentrated to afford the crude product 5-bromo-3-(5-methyloxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine (0.500 g) as a solid. NMR Spectrum: (DMSOd6) 2.60 (s, 3H), 7.35 (d, 1H), 7.85 (bs, 2H), 8.10 (d, 1H), 8.35 (d, 1H), 8.37 (d, 1H); Mass spectrum: M+H+ 304-306.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. extractionThe reaction mixture was extracted with dichloromethane/acetonitrile
  3. washthe organic phase was washed with water
  4. dry with materiala saturated aqueous solution of brine, dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2be1f258f0648df84ae2333af33b771
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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