Dimethylformamide → HCID 71020563, compound

HRID 1455269Notes

Reaction equation

HRID 1455269 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-].[K+].[K+].C(O[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([O:17][C:18](C)([CH3:20])[CH3:19])=O.C[N:31](C)[CH:32]=[O:33]>>[CH:18]([O:17][CH:7]([CH3:6])[CH3:2])([CH3:20])[CH3:19].[C:1]([C:2]1[CH:7]=[CH:6][C:5]([O:12][C:9]2[C:32](=[O:33])[NH:31][N:8]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:1]=2[CH2:2][CH3:3])=[CH:4][CH:3]=1)#[N:8]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7505BenzonitrileHCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonate

Product 2

HCID 7914Diisopropyl EtherHCID 71020563HCID 71020563, compoundYield 73%

Conditions

Temperature
50 °C

Procedure

To a stirred solution of the benzonitrile of Preparation 15 (800 mg, 3.5 mmol) in N,N-dimethylformamide (10 ml), under nitrogen, were added potassium carbonate (580 mg, 4.2 mmol) and di-tert-butyl dicarbonate (915 mg, 4.2 mmol), dissolved in N,N-dimethylformamide (10 ml). The reaction mixture was stirred at 50° C. for 6 hours. It was then partitioned between ethyl acetate (100 ml) and water (200 ml). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×50 ml). The organic extracts were combined, dried over magnesium sulphate, filtered and evaporated to give a pale orange solid, which was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume). Trituration of the solid with diisopropyl ether:pentane provided the title compound as a cream coloured solid (842 mg, 73%).

Workup

  1. customIt was then partitioned between ethyl acetate (100 ml) and water (200 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×50 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a pale orange solid, which
  8. customwas purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume)

Sources & evidence

ORD record
ord-1c072ea4ac7f4a57bfbc452e7c685f27
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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