Ethyl Acetate → HCID 57757929, compound

HRID 229618Notes

Reaction equation

HRID 229618 reaction equation
[H-].[Li+].[NH2:3][C:4]1[C:9]2=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[C:11]([CH:13]=O)=[CH:12][N:8]2[N:7]=[CH:6][N:5]=1.C([O-])(O)=O.[Na+].[CH3:29][CH2:30][O:31][C:32]([CH3:34])=[O:33]>C1COCC1>[NH2:3][C:4]1[C:9]2=[C:10]([C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)[C:11](/[CH:13]=[CH:34]/[C:32]([O:31][CH2:30][CH3:29])=[O:33])=[CH:12][N:8]2[N:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62714Lithium hydrideHCID 516892Sodium BicarbonateHCID 57757971HCID 57757971, compound

Product 1

HCID 57757929HCID 57757929, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium hydride (68 mg, 4.0 mmol) in THF (5 mL) under N2 atmosphere was added triethyl phosphonoacetate (498 mg, 2.22 mmol). The mixture was stirred at rt for 30 min and to the reaction mixture was added a slurry of 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carbaldehyde (433 mg, 1.53 mmol) in THF (15 ml). The mixture was heated at reflux for 2 h. After it was cooled to rt, aqueous NaHCO3 was slowly added followed by EtOAc. The organic layer was collected and the aqueous layer was back extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4) and evaporated to give a crude yellow solid that was purified by column chromatography (10:90 to 90:10 v/v EtOAc-hexanes) to afford the title compound (480 mg, 89%). 1H-NMR (CD3OD) δ 8.42 (d, J=8.0 Hz, 2H), 8.17 (s, 1H), 7.88 (s, 1H), 7.68 (d, J=8.0 Hz, 2H), 7.43 (d, J=16 Hz, 1H), 6.36 (d, J=16 Hz, 1H), 4.16 (q, J=7.1 Hz, 2H), 1.23 (t, J=7.1 Hz, 3H); MS [M+H]+=354; LCMS RT=3.12 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter it was cooled to rt
  4. customThe organic layer was collected
  5. extractionthe aqueous layer was back extracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customevaporated
  8. customto give a crude yellow solid
  9. customthat was purified by column chromatography (10:90 to 90:10 v/v EtOAc-hexanes)

Sources & evidence

ORD record
ord-37cfb981de624fb09e843583287aeb4f
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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