Ammonia methanol → HCID 86721492, compound

HRID 869623Notes

Reaction equation

HRID 869623 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=[C:16]([F:22])[C:17](OCC)=[O:18])[C:7]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:8]=3[O:9][CH2:10][C:4]=2[CH:3]=1.CO.[NH3:27]>C1COCC1>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=[C:16]([F:22])[C:17]([NH2:27])=[O:18])[C:7]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:8]=3[O:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 86721491HCID 86721491, compound

Product 1

HCID 86721492HCID 86721492, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

[step 2] Ethyl 2-(8-bromo-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-2-fluoroacetate (1.6 g, 4.05 mmol) obtained in step 1 was dissolved in THF (14 mL), 2 mol/L ammonia methanol solution (20 mL, 40.5 mmol) was added, and the mixture was stirred at 55° C. overnight. The mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 v/v) to give 2-(8-bromo-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)-2-fluoroacetamide (910 mg, 61%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 v/v)

Sources & evidence

ORD record
ord-61d8058cf0a64af1bf363e4d393520c2
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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