Acetic Anhydride → HCID 68278911, compound

HRID 508202Notes

Reaction equation

HRID 508202 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[C:10]([F:15])[CH:11]=[CH:12][CH:13]=2)[C:8]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[C:18]([OH:25])[CH:17]=2)=[N:7]1)=[O:5].[CH3:34][C:35](OC(C)=O)=[O:36].[Mg+2].[I-].[I-]>C(OCC)C>[C:35]([O:25][C:18]1[CH:17]=[C:16]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][C:10]=3[F:15])[N:6]([C:4](=[O:5])[C:3]3[C:26]([C:30]([F:32])([F:31])[F:33])=[CH:27][CH:28]=[CH:29][C:2]=3[Cl:1])[N:7]=2)[CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])(=[O:36])[CH3:34]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 5462737Magnesium diiodideHCID 68278907HCID 68278907, compound

Product 1

HCID 68278911HCID 68278911, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of compound 26A (48 mg, 0.1 mmol), Ac2O (0.8 mL) and MgI2 (28 mg, 0.1 mmol) in anhydrous ethyl ether (3 mL) was refluxed at 40° C. for 0.5 h. The reaction was cooled to rt, quenched with H2O, extracted with ether, and concentrated. The crude product was dissolved in THF (10 mL)/H2O (10 mL) and refluxed at 80° C. for 1 h. The mixture was cooled to rt, diluted with H2O, and extracted with EtOAc. The combined organic extracts were concentrated and purified by flash chromatography PE/EA (5/1) to give the title compound as a white solid. LCMS (ESI): calc'd for C22H12ClF4N2O4 [M+H]+: 521. found: 521, 1H NMR (400 MHz, MeOD) δ 8.47 (1H, d, J=8.0 Hz), 8.11 (1H, d, J=8.0 Hz), 7.90-7.76 (5H, m), 7.53 (1H, t, J=1.6 Hz), 3.34 (1H, q, J=8.0 Hz), 2.31 (3H, s).

Workup

  1. temperatureThe reaction was cooled to rt
  2. customquenched with H2O
  3. extractionextracted with ether
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in THF (10 mL)/H2O (10 mL)
  6. temperaturerefluxed at 80° C. for 1 h
  7. temperatureThe mixture was cooled to rt
  8. additiondiluted with H2O
  9. extractionextracted with EtOAc
  10. concentrationThe combined organic extracts were concentrated
  11. custompurified by flash chromatography PE/EA (5/1)

Sources & evidence

ORD record
ord-4269aaf3adb445d1984adadd9228f272
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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