Potassium Carbonate → HCID 71270936, compound

HRID 1525885Notes

Reaction equation

HRID 1525885 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[F:14])[C:3]([NH:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[CH:22]1([N:25]2[CH2:30][C:29]3([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[O:28][CH2:27][C:26]2=[O:36])[CH2:24][CH2:23]1>CN(C)C=O.O>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH:2]([N:33]2[CH2:34][CH2:35][C:29]3([O:28][CH2:27][C:26](=[O:36])[N:25]([CH:22]4[CH2:23][CH2:24]4)[CH2:30]3)[CH2:31][CH2:32]2)[C:3]([NH:5][CH3:6])=[O:4])=[C:8]([F:14])[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69083351HCID 69083351, compoundHCID 867254242-bromo-2-(4-bromo-2-fluorophenyl)-N-methylacetamide

Product 1

HCID 71270936HCID 71270936, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-2-(4-bromo-2-fluorophenyl)-N-methylacetamide (0.579 mmol) in N,N-dimethylformamide (3 mL) was treated with potassium carbonate (1.715 mmol) and 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (0.632 mmol). The reaction was allowed to stir at room temperature overnight. The reaction solution was then diluted with water (50 mL) and was extracted three times with dichloromethane. The organic layers were combined and were washed with water three times, twice with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-6% methanol/dichloromethane) afforded the title compound as a yellow oil (185 mg, 63% yield). MS(ES)+ m/e 454.0/455.9 [M+H]+ (bromide isotope pattern).

Workup

  1. extractionwas extracted three times with dichloromethane
  2. washwere washed with water three times, twice with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel chromatography (0-6% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ab07ee3e707646469e07aebc15b2c349
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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