Chloroacetone → 1-(2'-amino-7-bromo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yloxy)propan-2-one

HRID 335813

Reaction equation

HRID 335813 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([OH:20])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([Br:21])=[CH:10][CH:11]=3)[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30](=[O:32])[CH3:31].O.[Cl-].[Na+].O>CN(C=O)C.C1COCC1>[NH2:1][C:2]1[O:3][CH2:4][C:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([O:20][CH2:29][C:30](=[O:32])[CH3:31])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([Br:21])=[CH:10][CH:11]=3)[N:6]=1

Participants

7

Reactant 4

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 23713072Sodium chloride dihydrateHCID 584662822'-amino-7-bromo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-3-ol

Product 1

HCID 673830821-(2'-amino-7-bromo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yloxy)propan-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2′-amino-7-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-3-ol (0.570 g, 1.637 mmol) in 5 mL DMF was treated with potassium carbonate (0.283 g, 2.047 mmol) and was allowed to stir at RT for 15 minutes. The reaction mixture was then cooled to 0° C. and 1-chloropropan-2-one (0.151 g, 1.637 mmol) was added as a solution in 1 mL THF. After stirring for one hour the reaction mixture was allowed to warm to RT and stir for 4 hours. The reaction mixture was poured into 1:1 water/brine, extracted with EtOAc (3×25 mL). The combined organics were dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography provided 1-(2′-amino-7-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-3-yloxy)propan-2-one. MS m/z=404.0 [M+H].

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. stirringAfter stirring for one hour the reaction mixture
  3. temperatureto warm to RT
  4. stirringstir for 4 hours
  5. extractionextracted with EtOAc (3×25 mL)
  6. dry with materialThe combined organics were dried over MgSO4
  7. concentrationconcentrated
  8. customPurification of the crude residue by column chromatography

Sources & evidence

ORD record
ord-61ec904ad3f34565878323b55291e9a0
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Linked notes

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