Potassium Carbonate → HCID 118101200, compound

HRID 708875Notes

Reaction equation

HRID 708875 reaction equation
[F:1][C:2]1[C:3]([OH:21])=[C:4]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Br[CH2:23][C:24]([CH:26]1[CH2:28][CH2:27]1)=[O:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:26]1([C:24](=[O:25])[CH2:23][O:21][C:3]2[C:2]([F:1])=[CH:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][C:4]=2[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 109208412-Bromo-1-cyclopropylethan-1-oneHCID 70292396HCID 70292396, compound

Product 1

HCID 118101200HCID 118101200, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 17D (1.15 g, 3.83 mmol) in DMF (10 mL) was added 21A (1.486 g, 3.69 mmol), K2CO3 (2.65 g, 19.15 mmol). The mixture was stirred 60° C. for 2 h, quenched with water, extracted with EtOAc (2×). The extract was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography to give 21B (1.486 g, 3.69 mmol, 96% yield). MS (ESI) m/z: 383.2 (M+H)+.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6c9980a35c704b919976c10553268e6c
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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