Ammonium formate → HCID 25227426, compound

HRID 402866Notes

Reaction equation

HRID 402866 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[O:8][CH:7]=2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[O:8][CH2:7]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 110858754'-Fluoroisoflavone

Product 1

HCID 25227426HCID 25227426, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared according to the general procedure using 4′-fluoroisoflavone (77 mg, 0.319 mmol), ammonium formate (81 mg, 1.28 mmol), methanol (6.4 mL) and 10% Pd/C (81 mg). Purified by flash column chromatography (SiO2, 10% EtOAc/Hex) to afford 46 (18 mg, 23%) as an off-white solid. Analytical data for isoflavanone 46: 1H NMR (500 MHz, CDCl3) δ 7.97 (d, J=9.5 Hz, 1H), 7.53 (app t, J=9 Hz, 1H), 7.29-7.26 (m, 2H), 7.09-7.03 (m, 3H), 4.70-4.62 (m, 2H), 4.02-3.99 (m, 1H); 13C NMR (125 MHz, CDCl3) δ 205.8, 192.2, 191.9, 161.8, 136.4, 130.9, 130.5, 128.0, 122.0, 121.1, 118.1, 116.2, 116.0, 71.6, 51.8; LCMS: Mass calculated for C15H11FO2, [M+H]+, 243. Found 243.

Workup

  1. customPrepared
  2. customPurified by flash column chromatography (SiO2, 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-cada1917261044789d0b4d90abb7cac3
Source dataset
uspto-grants-2014_06
Patent number
US08742141B2

Reaction notes

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