Trimethylsilyl iodide → HCID 86762760, compound

HRID 876728Notes

Reaction equation

HRID 876728 reaction equation
I[Si](C)(C)C.[C:6]([NH:14][C:15]1[S:16][CH2:17][CH:18]2[CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH2:21][C:19]2([C:34]2[CH:39]=[C:38]([Br:40])[CH:37]=[CH:36][C:35]=2[F:41])[N:20]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(#N)C>[NH3:14].[Br:40][C:38]1[CH:37]=[CH:36][C:35]([F:41])=[C:34]([C:19]23[CH2:21][NH:22][CH2:23][CH:18]2[CH2:17][S:16][C:15]([NH:14][C:6](=[O:13])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:20]3)[CH:39]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86762759Benzyl 2-benzamido-7a-(5-bromo-2-fluoro-phenyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 2

HCID 222AmmoniaHCID 86762760HCID 86762760, compoundYield 187.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (2.21 mL, 15.46 mmol) is added drop wise to a room temperature solution of benzyl 2-benzamido-7a-(5-bromo-2-fluoro-phenyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (2.93 g, 5.15 mmol) in acetonitrile (44 mL). The reaction is stirred at room temperature for two hours and the solvent is removed in vacuo. The crude product is purified with an SCX column using 3:1 dichloromethane:methanol and then 2:1 dichloromethane:7 N ammonia in methanol to give the title compound (2.098 g, 94%). ES/MS (m/e): (79Br/81Br) 434/436 (M+H).

Workup

  1. customthe solvent is removed in vacuo
  2. customThe crude product is purified with an SCX column

Sources & evidence

ORD record
ord-3e51899180064b2b8b53c3d9f3c8c07a
Source dataset
uspto-grants-2015_03
Patent number
US08987254B2

Reaction notes

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