Ammonium formate → HCID 23157422, compound

HRID 1827592Notes

Reaction equation

HRID 1827592 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[CH:27]=2)[S:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])(=[O:15])=[O:14])=[CH:8][CH:7]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[CH:27]=2)[S:13]([C:16]2[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])(=[O:14])=[O:15])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 69591801HCID 69591801, compound

Product 1

HCID 23157422HCID 23157422, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid methyl ester (0.252 g, 0.46 mmol) in methanol was added palladium black (catalytic amount) and ammonium formate (0.289 g, 4.58 mmol). The reaction mixture was stirred at 60° C. for 24 hr. Additional palladium black (catalytic amount) and ammonium formate (0.289 g, 4.58 mmol) were added and the reaction mixture was stirred at 60° C. for 24 hr. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed with water and saturated aqueous sodium bicarbonate. The aqueous solution was washed with methylene chloride. The organic layer was concentrated to afford 0.172 g of the title compound of Step A. 1H NMR (CDCl3) δ 7.10–7.05 (m, 1H), 7.00–6.90 (m, 4H), 6.89–6.80 (m, 4H), 6.75–6.70 (m, 1H), 5.27–5.25 (m, 1H), 4.80–4.70 (m, 2H), 3.85–3.75 (m, 1H), 3.60 (s, 3H), 3.55–3.50 (m, 1H), 2.82 (t, 2H, J=7.6 Hz), 2.53 (t, 2H, J=6.8 Hz), 2.43 (s, 6H), 2.26 (s, 3H), 2.00–1.90 (m, 1H), 1.85–1.75 (m, 2H) 1.65–1.50 (m, 3H).

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 24 hr
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washthe filter cake was washed with water and saturated aqueous sodium bicarbonate
  4. washThe aqueous solution was washed with methylene chloride
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-e6243c3a5480455e8905549717b5b310
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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