Water → HCID 67388498, compound

HRID 908419Notes

Reaction equation

HRID 908419 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.Cl.[NH2:13][C:14]1[C:19](O)=[CH:18][C:17]([F:21])=[CH:16][N:15]=1.O>C[Si](OP(=O)=O)(C)C>[Br:11][C:5]1[CH:6]=[C:7]([C:8]2[O:10][C:19]3[C:14]([N:13]=2)=[N:15][CH:16]=[C:17]([F:21])[CH:18]=3)[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7374452-Amino-5-bromonicotinic acidHCID 119096305HCID 119096305, compound

Product 1

HCID 67388498HCID 67388498, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 16133246Trimethyl(phosphooxy)silaneSolvent

Conditions

Temperature
100 °C

Procedure

2-amino-5-bromo-pyridine-3-carboxylic acid (797 mg) and 2-amino-5-fluoro-pyridin-3-ol, hydrochloride (400 mg) powders were mixed together and the resulting mixture was portionwise added in trimethylsilyl polyphosphate (4.5 g) stirred at 100° C. The mixture was stirred at 140° C. overnight. After cooling, water (20 ml) was added. The resulting precipitate was collected by filtration, washed with a 2N aqueous solution of HCl and water. The resulting solid was triturated in Ethyl acetate, collected by filtration to afford 5-bromo-3-(6-fluorooxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine (150 mg). NMR Spectrum: (DMSO-d6) 7.10 (bs, 2H), 7.66 (dd, 1H), 8.31 (d, 1H), 8.39 (d, 1H), 8.49 (dd, 1H); Mass spectrum: M+H+ 309-311.

Workup

  1. stirringThe mixture was stirred at 140° C. overnight
  2. temperatureAfter cooling
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with a 2N aqueous solution of HCl and water
  5. customThe resulting solid was triturated in Ethyl acetate
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-677f0f980fa849a692397680f47ea601
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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