Isobutyl iodide → HCID 69491400, compound

HRID 1296742Notes

Reaction equation

HRID 1296742 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:33][CH3:34])[C:31]=1[CH3:32])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[CH:12][C:11]=1[NH:22]C(=O)C(F)(F)F)=[O:7].[CH2:35](I)[CH:36]([CH3:38])[CH3:37].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.CO.O>[CH2:35]([NH:22][C:11]1[CH:12]=[C:13]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)[CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:29]=[C:30]([O:33][CH3:34])[C:31]([CH3:32])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH:36]([CH3:38])[CH3:37]

Participants

8

Reactant 3

HCID 10556Isobutyl iodide2×HCID 11430Potassium Carbonate2×HCID 86595900HCID 86595900, compound

Product 1

HCID 69491400HCID 69491400, compoundYield 54.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of compound 1h (200 mg, 0.42 mmol), isobutyl iodide (0.144 mL, 1.25 mmol), and potassium carbonate (173 mg, 1.25 mmol) in DMF (2 mL) was sealed in a pressure tube and heated at 85° C. for three days. Additional portions of isobutyl iodide (3 eq) were added each day. The reaction mixture was cooled to rt, diluted with ethyl acetate, washed with water and brine, dried, and concentrated on a rotary evaporator. The residue was dissolved in a mixture of methanol (10 mL) and water (1 mL), and potassium carbonate (200 mg, 1.45 mmol) was added. The reaction mixture was heated at 50° C. for 2 h. The reaction mixture was diluted with water, filtered, and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel (35% v/v ethyl acetate/hexane) to give compound 7a (100 mg, 54%) as a pale yellow solid. ESI-MS m/e 439.3 (M+1).

Workup

  1. customwas sealed in a pressure tube
  2. temperatureThe reaction mixture was cooled to rt
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated on a rotary evaporator
  6. additionwas added
  7. temperatureThe reaction mixture was heated at 50° C. for 2 h
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. customThe residue was purified by chromatography on silica gel (35% v/v ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6172cb0b268c48bba50c9475136185cc
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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