Dimethylformamide → HCID 71168396, compound

HRID 2282458Notes

Reaction equation

HRID 2282458 reaction equation
Cl.[CH3:2][C:3]([CH3:8])([CH3:7])[C:4]([NH2:6])=O.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=O.C([O-])([O-])=O.[K+].[K+].C[N:27](C=O)C>>[C:3]([C:4]1[NH:27][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:10][N:6]=1)([CH3:8])([CH3:7])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 692722-Bromo-4'-methylacetophenoneHCID 12229410HCID 12229410, compound

Product 1

HCID 71168396HCID 71168396, compoundYield 49%

Conditions

Temperature
75 °C

Procedure

A red suspension of 2,2-dimethylpropionamide hydrochloride (Atlantic, 1.00 g, 7.32 mmol), 2-bromo-4′-methylacetophenone (Aldrich, 1.56 g, 7.32 mmol) and K2CO3 (1.52 g, 11.0 mmol) in DMF (20 mL) was stirred at 75° C. for 3 h. The mixture was cooled to RT, concentrated in vacuo, suspended in water (25 mL) and extracted with DCM (2×25 mL). The combined organics were passed through a hydrophobic frit, concentrated in vacuo, redissolved in MeOH (5 mL), applied to an SCX-2 cartridge (20 g) and washed with MeOH (100 mL). The product was eluted with 2M NH3 in MeOH (60 mL); concentration in vacuo left a yellow foam (1.26 g). FCC, using 1-5% MeOH in DCM, gave the title compound as a pale yellow solid (770 mg, 49%). LCMS (Method 3): Rt 2.26 min, m/z 215 [MH+].

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. extractionextracted with DCM (2×25 mL)
  4. concentrationconcentrated in vacuo
  5. dissolutionredissolved in MeOH (5 mL)
  6. washwashed with MeOH (100 mL)
  7. washThe product was eluted with 2M NH3 in MeOH (60 mL)
  8. concentrationconcentration in vacuo
  9. waitleft a yellow foam (1.26 g)

Sources & evidence

ORD record
ord-c15cf8b876ee47f4a7130d3dfcede561
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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