Potassium Carbonate → HCID 66678163, compound

HRID 2410558Notes

Reaction equation

HRID 2410558 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:10][O:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH2:15][N:14]([CH2:13][CH2:12][O:11][CH3:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[CH:17][CH:18]=1)#[N:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 28426087HCID 28426087, compound

Product 1

HCID 66678163HCID 66678163, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl bromoacetate (1.64 mL, 11.1 mmol) was added into a mixture of 4-{[(2-methoxyethyl)amino]methyl}benzonitrile (958 mg, 5.04 mmol) and K2CO3 (3.06 g, 22.2 mmol) in ACN (20 mL). The resulting mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc, and then washed with water and brine, dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (silica, cHex/EtOAc) to give the title compound as a colorless oil. LC/MS (Method B): 305.1 (M+H)+. HPLC (Method A) Rt 3.09 min (Purity: 91.1%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica, cHex/EtOAc)

Sources & evidence

ORD record
ord-5148acc93e494533a63ec7081b77e95c
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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