Methanol → HCID 71053005, compound

HRID 869919Notes

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[CH:28]=[C:27]([CH3:29])[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.[Si](I)(C)(C)C.CO.C(OCC)(=O)C>CC#N.O>[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[CH:28]=[C:27]([CH3:29])[NH:26][C:25](=[O:30])[CH:24]=5)[N:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-methoxy-3,6′-dimethyl-2,4′-bipyridin-6-yl)cyclopropanecarboxamide (12 mg, 26.5 μmol) in CH3CN (0.5 mL) was added TMSI (7.5 μL, 52.9 μmol) drop wise. The reaction was stirred at 55° C. for 1 hour. MeOH (1.0 mL) was added followed by ethyl acetate (3 mL) and water (1 mL). The organic layer was separated and washed with NaHSO3 (2×), and brine (1×). The organic layer was then dried over Na2SO4, filtered and evaporated under reduced pressure to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5-methyl-6-(6-methyl-2-oxo-1,2-dihydropyridin-4-yl)pyridin-2-yl)cyclopropanecarboxamide as a white solid (9.5 g, 81.7%); ESI-MS m/z calc. 439.4. found 440.5 (M+1)+. Retention time 1.60 minutes.

Workup

customThe organic layer was separated
washwashed with NaHSO3 (2×), and brine (1×)
dry with materialThe organic layer was then dried over Na2SO4
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-d6041d131a4f4838b2d5ddbaf447c5ec
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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