Trimethylsilyl iodide → HCID 71053076, compound

HRID 869980Notes

Reaction equation

HRID 869980 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:28]([F:29])=[CH:27][N:26]=[C:25]([O:30]C)[CH:24]=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:28]([F:29])=[CH:27][NH:26][C:25](=[O:30])[CH:24]=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 710530741-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5'-fluoro-2'-methoxy-3-methyl-2,4'-bipyridin-6-yl)cyclopropanecarboxamide

Product 1

HCID 71053076HCID 71053076, compoundYield 47%

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-2,4′-bipyridin-6-yl)cyclopropanecarboxamide (19 mg, 0.04 mmol) in chloroform (0.5 mL) was added iodotrimethylsilane (32 mg, 0.16 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 (5.1 mg, 47%). ESI-MS m/z calc. 443.38. found 444.3 (M+1)+. Retention time 1.63 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-8ba1c941a596458789d66f957b45ccf6
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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