Trimethylsilyl iodide → HCID 68739988, compound

HRID 869964Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:27]2[CH:28]=[N:29][C:30]([O:33]C)=[CH:31][CH:32]=2)=[N:5][C:6]([NH:10][C:11]([C:13]2([C:16]3[CH:26]=[CH:25][C:19]4[O:20][C:21]([F:24])([F:23])[O:22][C:18]=4[CH:17]=3)[CH2:15][CH2:14]2)=[O:12])=[CH:7][C:8]=1[CH3:9])#[N:2].I[Si](C)(C)C>C(#N)C>[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][C:11]([C:13]2([C:16]3[CH:26]=[CH:25][C:19]4[O:20][C:21]([F:24])([F:23])[O:22][C:18]=4[CH:17]=3)[CH2:14][CH2:15]2)=[O:12])=[N:5][C:4]=1[C:27]1[CH:32]=[CH:31][C:30](=[O:33])[NH:29][CH:28]=1)#[N:2]

Participants

Conditions

Temperature: 55 °C

Procedure

N-(3-cyano-6′-methoxy-4-methyl-2,3′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (0.150 g, 0.323 mmol) was dissolved in acetonitrile (7.2 mL). Iodotrimethylsilane (129.3 mg, 92 μL, 0.65 mmol) was added and the reaction mixture was heated to 55° C. for 5 hours. The crude reaction mixture was then evaporated to dryness, re-dissolved in a minimum of dichloromethane and purified on 12 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes (0.125 g, 86%). ESI-MS m/z calc. 450.1. found 451.1 (M+1)+. Retention time 1.60 minutes. 1H NMR (400 MHz, CDCl3) 8.17 (s, 1H), 8.07-8.03 (m, 2H), 7.82 (s, 1H), 7.26 (dd, J=1.7, 8.2 Hz, 1H), 7.19-7.16 (m, 2H), 6.69 (d, J=10.4 Hz, 1H), 2.58 (s, 3H), 1.80-1.75 (m, 2H), 1.27-1.22 (m, 2H).

Workup

customThe crude reaction mixture
customwas then evaporated to dryness
dissolutionre-dissolved in a minimum of dichloromethane
custompurified on 12 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes (0.125 g, 86%)

Sources & evidence

ORD record: ord-e185100d675a41f79272931546924d7c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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