Potassium Carbonate → HCID 71270849, compound

HRID 1525907Notes

Reaction equation

HRID 1525907 reaction equation
[C:1]([O:4][CH2:5][CH:6](Br)[C:7]1[C:12]([F:13])=[CH:11][C:10]([Br:14])=[CH:9][C:8]=1[F:15])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH:24]1([N:27]2[CH2:32][C:31]3([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[O:30][CH2:29][C:28]2=[O:38])[CH2:26][CH2:25]1>CN(C)C=O.O>[C:1]([O:4][CH2:5][CH:6]([C:7]1[C:12]([F:13])=[CH:11][C:10]([Br:14])=[CH:9][C:8]=1[F:15])[N:35]1[CH2:36][CH2:37][C:31]2([O:30][CH2:29][C:28](=[O:38])[N:27]([CH:24]3[CH2:25][CH2:26]3)[CH2:32]2)[CH2:33][CH2:34]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69083351HCID 69083351, compoundHCID 867254272-Bromo-2-(4-bromo-2,6-difluorophenyl)ethyl acetate

Product 1

HCID 71270849HCID 71270849, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-2-(4-bromo-2,6-difluorophenyl)ethyl acetate (1.013 mmol) in N,N-dimethylformamide (5 mL) was treated with potassium carbonate (3.04 mmol) and 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (1.115 mmol). The reaction was stirred at room temperature overnight. The reaction solution was diluted with water (100 mL) and was extracted three times with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude title compound as a yellow solid (405 mg of 80% pure material as estimated by 1H NMR, 65% yield). MS(ES)+ m/e 487.2/489.3 [M+H]+ (bromide isotope pattern).

Workup

  1. extractionwas extracted three times with diethyl ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de1b180e6e564e52a2290c73906a1bd4
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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