Sodium borohydride → 5-(1,3-Dioxolan-2-yl)-2-fluoro-3',5'-dimethoxybiphenyl-4-amine

HRID 56465Notes

Reaction equation

[F:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[CH:6][C:5]([CH:18]2[O:22][CH2:21][CH2:20][O:19]2)=[C:4]([N+:23]([O-])=O)[CH:3]=1.[BH4-].[Na+]>[Pd].C(O)C.O.C(OCC)(=O)C>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:5]1[C:4]([NH2:23])=[CH:3][C:2]([F:1])=[C:7]([C:8]2[CH:9]=[C:10]([O:16][CH3:17])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)[CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(6-fluoro-3′,5′-dimethoxy-4-nitrobiphenyl-3-yl)-1,3-dioxolane (1.8 g, 5.2 mmol), sodium borohydride (587.9 mg, 15.5 mmol) and 10% palladium on carbon (0.2 g) in ethanol/water (33 mL, v/v=10/1) was heated at 90° C. for 1 hour. After that, the mixture was diluted with ethyl acetate (150 mL), and washed by water (50 mL) and brine (50 mL). The organic layer was dried over sodium, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1 to 4/1) to afford the title compound (1.4 g, 88%) as a yellow solid. MS (ES+) C17H18FNO4 requires: 319, found: 320 [M+H]+.

Workup

washwashed by water (50 mL) and brine (50 mL)
dry with materialThe organic layer was dried over sodium
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1 to 4/1)

Sources & evidence

ORD record: ord-79dcf193974c411b9a5ca8d872515215
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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