Potassium Carbonate → 2-(4-Bromo-2-fluorophenyl)-2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl acetate

HRID 1525881Notes

Reaction equation

HRID 1525881 reaction equation
[C:1]([O:4][CH2:5][CH:6](Br)[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[F:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH:23]1([N:26]2[CH2:31][C:30]3([CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[O:29][CH2:28][C:27]2=[O:37])[CH2:25][CH2:24]1>CN(C)C=O.O>[C:1]([O:4][CH2:5][CH:6]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[F:14])[N:34]1[CH2:35][CH2:36][C:30]2([O:29][CH2:28][C:27](=[O:37])[N:26]([CH:23]3[CH2:24][CH2:25]3)[CH2:31]2)[CH2:32][CH2:33]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69083351HCID 69083351, compoundHCID 867254232-Bromo-2-(4-bromo-2-fluorophenyl)ethyl acetate

Product 1

HCID 712709352-(4-Bromo-2-fluorophenyl)-2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl acetateYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-2-(4-bromo-2-fluorophenyl)ethyl acetate (0.971 mmol) in N,N-dimethylformamide (5 mL) was treated with potassium carbonate (2.91 mmol) and 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (1.019 mmol). The reaction was allowed to stir at room temperature overnight. The reaction solution was then diluted with water (50 mL) and was extracted four times with ethyl acetate. The combined organic layer was washed four times with water, twice with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as an oil (385 mg, 76% yield). MS(ES)+ m/e 469.1/471.2 [M+H]+ (bromide isotope pattern).

Workup

  1. extractionwas extracted four times with ethyl acetate
  2. washThe combined organic layer was washed four times with water
  3. dry with materialtwice with brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4508b94348cb43c2821aa2dc95dd3f7d
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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