Trimethylsilyl iodide → HCID 178426546, compound

HRID 1442833Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxypyrimidin-5-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide (88 mg, 0.20 mmol) in CH3CN (2 mL) was added TMSI (80 mg, 0.40 mmol). The mixture was heated at 75° C. for 4 hours. The mixture was partitioned between ethyl acetate and H2O, and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by preparative LC/MS to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(2-hydroxypyrimidin-5-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide. MS (ESI) m/e (M+H+) 427.3.

Workup

customThe mixture was partitioned between ethyl acetate and H2O
extractionthe aqueous layer was extracted with ethyl acetate (3×)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative LC/MS

Sources & evidence

ORD record: ord-adb25a99d7d84234b9d49d32fa9717fa
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659268B2

Reaction notes

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