Potassium Carbonate → HCID 67388453, compound

HRID 908429Notes

Reaction equation

HRID 908429 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[O:9][C:10]3[C:11](=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][C:5]([Br:18])=[CH:4][N:3]=1.[C:19](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:18][C:5]1[CH:6]=[C:7]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:19])[C:11]=3[N:12]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67388904HCID 67388904, compound

Product 1

HCID 67388453HCID 67388453, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

TFA (20 ml) was added to the mixture. The resulting solution was stirred at 25° C. for 2 hours. The TFA was evaporated and the mixture was basified with a solution 7N of ammonia in methanol. The mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 1 to 2% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(2-amino-5-bromo-3-pyridyl)-1,3-benzoxazol-4-ol (1.040 g) as a solid. NMR Spectrum: (DMSOd6) 6.81 (d, 1H), 7.18 (d, 1H), 7.25 (dd, 1H), 7.94 (bs, 2H), 8.28 (d, 1H), 8.30 (d, 1H), 10.47 (bs, 1H); Mass spectrum: M+H+ 306-308 Iodomethane (0.5 ml) was added to a stirred suspension 2-(2-amino-5-bromo-3-pyridyl)-1,3-benzoxazol-4-ol (820 mg) and potassium carbonate (1111 mg) in DMF (5 ml). The resulting suspension was stirred at 25° C. for 3 hours. The DMF was evaporated under reduce pressure. The mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 5-bromo-3-(4-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine (480 mg) as a solid. NMR Spectrum: (CDCl3) 4.08 (s, 3H), 6.84 (d, 1H), 6.93 (bs, 2H), 7.20 (d, 1H), 7.31 (dd, 1H), 8.23 (d, 1H), 8.38 (d, 1H); Mass spectrum: M+H+ 319-321

Workup

  1. customThe DMF was evaporated
  2. customThe crude product was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in dichloromethane
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-c3c7b704bcbf482684d6cca8c5d62e8b
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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