Iodoethane → HCID 57438797, compound

HRID 2263504Notes

Reaction equation

[F:1][C:2]1[C:10]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].I[CH2:18][CH3:19].[BH4-].[Na+]>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:18]([N:14]1[CH2:15][CH:16]=[C:11]([C:10]2[C:2]([F:1])=[C:3]([CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:6])=[O:5])[CH2:12][CH2:13]1)[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To neat 2-fluoro-3-pyridin-4-yl-benzamide (0.94 g, 4.34 mmol) was added 1-iodoethane (3 ml) and the resulting mixture was heated at 100° C. for 2 h. Excess 1-iodopropane was evaporated under reduced pressure and ethanol (40 ml) was added. The mixture was cooled to −20° C. and sodium borohydride (1.25 g, 34.8 mmol) was added in portions. The resulting mixture was stirred for 1 h, after which aqueous sodium carbonate (10%, 50 ml) was added. The aqueous phase was extracted with ethylacetate (3×100 ml) and the combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (ethylacetate/methanol, 1:1) to give the title compound (0.75 g). MS m/z (rel. intensity, 70 eV) 248 (M+, bp), 247 (37), 233 (99), 146 (22), 110 (41).

Workup

customExcess 1-iodopropane was evaporated under reduced pressure and ethanol (40 ml)
additionwas added
temperatureThe mixture was cooled to −20° C.
extractionThe aqueous phase was extracted with ethylacetate (3×100 ml)
dry with materialthe combined organic phases was dried (MgSO4)
filtrationfiltered
customevaporated to dryness
customThe residue was purified by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record: ord-ceb6fe2c54c84681b6e2f91c06073b6b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851629B2

Reaction notes

Loading…