Ammonium Acetate → HCID 67383124, compound

HRID 335888Notes

Reaction equation

HRID 335888 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15]([CH2:17][C:18]([F:23])([F:22])[C:19]([NH2:21])=[O:20])(O)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:24][CH3:25])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.C([O-])(=O)C.[NH4+]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:17][C:18]([F:23])([F:22])[C:19](=[O:20])[NH:21]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:24][CH3:25])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67383079HCID 67383079, compound

Product 1

HCID 67383124HCID 67383124, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-(3-bromo-5-hydroxy-7-methoxy-5H-chromeno[2,3-b]pyridin-5-yl)-2,2-difluoropropanamide (0.120 g, 0.289 mmol) was added to a saturated solution of ammonium acetate (2.228 g, 28.9 mmol) in 2-propanol (20 mL) and the mixture was heated to reflux. After 2.5 hours the reaction was allowed to cool to rt and the 2-propanol was removed in vacuo. The derived residue was partitioned between CH2Cl2 (50 mL) and water (50 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×25 mL) and EtOAc (3×25 mL). The combined organic layers were washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, and concentrated. The product was precipitated from 1:1 chloroform and diethyl ether to afford 3-bromo-4′,4′-difluoro-7-methoxyspiro[chromeno[2,3-b]pyridine-5,2′-pyrrolidin]-5′-one as a gold solid. MS m/z=397.1 [M+H].

Workup

  1. temperaturethe mixture was heated to reflux
  2. customthe 2-propanol was removed in vacuo
  3. customThe derived residue was partitioned between CH2Cl2 (50 mL) and water (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (3×25 mL) and EtOAc (3×25 mL)
  6. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe product was precipitated from 1:1 chloroform and diethyl ether

Sources & evidence

ORD record
ord-004cc6c3f9544bf9a25ddf238a6877f8
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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