Methyl iodide → HCID 178485934, compound

HRID 2047487Notes

Reaction equation

HRID 2047487 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([N:13]([CH3:43])[C:14]([N:16]([CH3:42])[C@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19]([C:29]([C@H:31]3[CH2:36][CH2:35][C@H:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:33][CH2:32]3)=[O:30])[CH2:18]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:46]C(C)([O-])C.[K+].CI>CN(C=O)C>[F:45][C:2]([F:44])([F:1])[C:3]1[CH:4]=[C:5]([N:13]([CH3:43])[C:14]([N:16]([CH3:42])[C@H:17]2[C@H:21]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:20][N:19]([C:29]([C@H:31]3[CH2:32][CH2:33][C@H:34]([N:37]([CH3:46])[S:38]([CH3:41])(=[O:39])=[O:40])[CH2:35][CH2:36]3)=[O:30])[CH2:18]2)=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178485935HCID 178485935, compound

Product 1

HCID 178485934HCID 178485934, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (0.23 g) obtained in Example 242 in DMF (7.0 mL) were added potassium tert-butoxide (0.079 g) and methyl iodide (0.055 mL) at 0° C. The mixture was stirred at room temperature for 12 hr, diluted with ice water, and extracted with ethyl acetate. The extract was washed with water, 1N aqueous potassium hydrogen sulfate solution and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane) to give the title compound (0.17 g, 70%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, 1N aqueous potassium hydrogen sulfate solution and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bbaa5204ae2a4eed97ebd005e0b89ccc
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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