Butyl iodide → HCID 20649191, compound

HRID 325248Notes

Reaction equation

HRID 325248 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[CH:6][C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28].C(=O)([O-])[O-].[K+].[K+].I[CH2:37][CH2:38][CH2:39][CH3:40]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][N:12]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:13][C:14]2[CH:15]=[C:16]([F:21])[CH:17]=[C:18]([F:20])[CH:19]=2)=[CH:6][C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 20649180HCID 20649180, compound

Product 1

HCID 20649191HCID 20649191, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution at ambient temperature under N2 of 4-(N-(3,5-difluorobenzyl)aminooxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester (254 mg, 0.640 mmol), prepared as in Example 1176 C, in DMF (2 mL) was added potassium carbonate (265 mg, 1.92 mmol) and 1-iodobutane (0.146 mL, 1.28 mmol). Reaction stirred vigorously at 80° C. overnight. Reaction diluted with EtOAc and washed with water and brine. Organic layer dried with Na2SO4, filtered, and concentrated in vacuo. Residue was purified by flash chromatography on silica gel eluting with 7% EtOAc/Hexanes to 30% EtOAc/Hexanes to afford the desired product. (44 mg, 15%). m/e (ESI) 454 (MH+)

Workup

  1. customReaction
  2. customReaction
  3. washwashed with water and brine
  4. dry with materialOrganic layer dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customResidue was purified by flash chromatography on silica gel eluting with 7% EtOAc/Hexanes to 30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-42bc436e46cd42a39f66ccfd7713e771
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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