Methanesulfonyl chloride → HCID 56602987, compound

HRID 1620312Notes

Reaction equation

HRID 1620312 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]1[C:18]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]([NH2:24])=[O:23])=[CH:17][CH:16]=[CH:15][N:14]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C1COCC1>[CH3:11][O:12][C:13]1[C:18]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]([NH:24][S:36]([CH3:35])(=[O:38])=[O:37])=[O:23])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 66666483HCID 66666483, compound

Product 1

HCID 56602987HCID 56602987, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium bis(trimethylsilyl)amide solution in THF (1 M, 0.78 mL, 0.78 mmol) was added to a solution of 3-(2-methoxypyridin-3-yl)-4-phenoxybenzamide (Preparation 19, 0.1 g, 0.31 mmol) in THF (4 mL) at room temperature and the reaction allowed to stir for 30 minutes. Methanesulfonyl chloride (0.088 g, 0.78 mmol) was added and the reaction was stirred at room temperature for 18 hours. The mixture was then partitioned between EtOAc (40 mL) and water (10 mL). The combined organics were dried over sodium sulfate and concentrated in vacuo to afford a brown solid. The crude product was purified by preparative HPLC to afford the title compound as a white solid (20 mg).

Workup

  1. stirringthe reaction was stirred at room temperature for 18 hours
  2. customThe mixture was then partitioned between EtOAc (40 mL) and water (10 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a brown solid
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-58702ed1a30547dba9fd02bbdced4c11
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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