Methyl iodide → HCID 53308301, compound

HRID 705436Notes

Reaction equation

HRID 705436 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([CH3:18])[S:16][CH:17]=2)=[CH:9][CH:8]=1)=[O:5].[C:27](O[K])(C)(C)C.CI>C1COCC1.CC(O)(C)C>[Cl:1][C:2]1[CH:22]=[C:21]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:20]=[CH:19][C:3]=1[C:4]([N:6]([CH3:27])[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([CH3:18])[S:16][CH:17]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 53255263HCID 53255263, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 53308301HCID 53308301, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-chloro-4-(methylsulfonyl)-N-(4-(2-methylthiazol-4-yl)phenyl)benzamide (50 mg, 0.123 mmol) in THF (1 mL) under nitrogen atmosphere was added 1M solution of tBuOK in tBuOH (0.14 mL) dropwise. After stirring for 15 min, CH3I (0.009 mL, 0.14 mmol) was added and the reaction mixture was stirred at 60° C. for 1 h, before partitioning between water and EtOAc. The organic layer was isolated, washed with brine, and adsorbed on silica. Purification on silica by flash chromatography using a gradient of 40-100% EtOAc/hexane yielded 40 mg of the titled compound as an off-white solid (77% yield).

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 1 h
  2. custombefore partitioning between water and EtOAc
  3. customThe organic layer was isolated
  4. washwashed with brine
  5. customPurification on silica by flash chromatography

Sources & evidence

ORD record
ord-4e3401e4e1c64d509d51d6298d0c48dc
Source dataset
uspto-grants-2015_11
Patent number
US09174949B2

Reaction notes

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