Methyl iodide → HCID 68843653, compound

HRID 660498Notes

Reaction equation

HRID 660498 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH:16][C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N:22]1[S:26](=[O:28])(=[O:27])[N:25]([CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:24](=[O:35])[CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:38]([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH:16][C:17]2[CH:21]=[N:20][N:19]([CH3:38])[CH:18]=2)[CH:12]=[CH:11][C:10]=1[N:22]1[S:26](=[O:27])(=[O:28])[N:25]([CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[C:24](=[O:35])[CH2:23]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68838915HCID 68838915, compound

Product 1

HCID 68843653HCID 68843653, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-{2-benzyloxy-4-[2-(1H-pyrazol-4-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (example 40, step C) (114 mg, 0.224 mmol), MeI (0.05 mL, 0.80 mmol) and K2CO3 (60 mg, 0.43 mmol) in CH3CN (3 mL) is stirred at RT for 2 days. The mixture is partitioned between EtOAc and aq. NaHCO3. The organic phase is dried over MgSO4 and concentrated to afford the crude product.

Workup

  1. customThe mixture is partitioned between EtOAc and aq. NaHCO3
  2. dry with materialThe organic phase is dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8c3ec823fca04f698dc2f99d5a16f566
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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