Trimethylsilyl iodide → HCID 71053075, compound

HRID 870000Notes

Reaction equation

HRID 870000 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]([NH:17][C:18]([C:20]3([C:23]4[CH:33]=[CH:32][C:26]5[O:27][C:28]([F:31])([F:30])[O:29][C:25]=5[CH:24]=4)[CH2:22][CH2:21]3)=[O:19])[N:11]=2)[C:5]([O:8]C)=[N:6][CH:7]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:11]=[C:12]([NH:17][C:18]([C:20]3([C:23]4[CH:33]=[CH:32][C:26]5[O:27][C:28]([F:30])([F:31])[O:29][C:25]=5[CH:24]=4)[CH2:22][CH2:21]3)=[O:19])[CH:13]=[CH:14][C:15]=2[CH3:16])[C:5](=[O:8])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 117640767HCID 117640767, compound

Product 1

HCID 71053075HCID 71053075, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To N-(5′-chloro-2′-methoxy-3-methyl-2,3′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (55 mg, 0.12 mmol) in chloroform (1 mL) was added iodotrimethylsilane (70 mg, 0.35 mmol). The reaction mixture was stirred at room temperature overnight. At this point the reaction mixture was purified directly by silica gel chromatography (eluting with a gradient of 0-5% methanol in dichloromethane) to yield the product (24 mg, 41%). ESI-MS m/z calc. 459.08. found 459.95 (MW+1)+. Retention time 1.62 minutes.

Workup

  1. customAt this point the reaction mixture was purified directly by silica gel chromatography (
  2. washeluting with a gradient of 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7dab8668062b4129959c983a15d964fb
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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