Trimethylsilyl iodide → HCID 71053057, compound

HRID 869994Notes

Reaction equation

HRID 869994 reaction equation
[F:1][C:2]1([F:33])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[C:24]([O:30]C)=[N:25][CH:26]=[C:27]([F:29])[CH:28]=5)[C:20]([CH3:32])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[F:33][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([CH3:32])=[C:21]([C:23]5[C:24](=[O:30])[NH:25][CH:26]=[C:27]([F:29])[CH:28]=5)[N:22]=4)=[O:15])[CH2:12][CH2:13]3)=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 1176411901-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5'-fluoro-2'-methoxy-3-methyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

Product 1

HCID 71053057HCID 71053057, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5′-fluoro-2′-methoxy-3-methyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (42 mg, 0.09 mmol) in chloroform (1 mL) was added iodotrimethylsilane (55 mg, 0.3 mmol). The reaction mixture was stirred at room temperature for three hours. At this point the reaction mixture was purified directly by silica gel chromatography (eluting with 0-100% ethyl acetate in hexanes) to yield the product (19 mg, 47%). ESI-MS m/z calc. 443.38. found 443.96 (M+1)+. Retention time 1.56 minutes.

Workup

  1. customAt this point the reaction mixture was purified directly by silica gel chromatography (eluting with 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5ea950b7ccb042eb9b1186203a285aa2
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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