Ammonium formate → HCID 16719865, compound

HRID 732825Notes

Reaction equation

HRID 732825 reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:17]=[CH:18][C:19]2[C:23]([O:24][C:25]3[CH:39]=[CH:38][C:28]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:27][CH:26]=3)=[C:22]([C:40]3[CH:45]=[CH:44][C:43]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH:42][CH:41]=3)[S:21][C:20]=2[CH:50]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:49][S:46]([C:43]1[CH:42]=[CH:41][C:40]([C:22]2[S:21][C:20]3[CH:50]=[C:16]([OH:15])[CH:17]=[CH:18][C:19]=3[C:23]=2[O:24][C:25]2[CH:39]=[CH:38][C:28]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:26]=2)=[CH:45][CH:44]=1)(=[O:47])=[O:48]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69076495HCID 69076495, compound

Product 1

HCID 16719865HCID 16719865, compoundYield 68.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve the compound of Example 90 (85 mg, 0.14 mmol) in methanol (14 mL) and ethyl acetate (14 mL). Add ammonium formate (262 mg, 4.2 mmol) and palladium hydroxide (90 mg) and heat to reflux for 1 hour. Filter the reaction mixture and concentrate in vacuo. Partition the residue between ethyl acetate:methanol (5:1, 6 mL) and saturated aqueous sodium bicarbonate:brine (1:1, 6 mL). Wash the organic layer with brine, and dry with sodium sulfate. Concentrate in vacuo to give 50 mg of the title compound (68%): 1H NMR (CDCl3): δ 7.85 (s, 4H), 7.18 (d, J=8.2 Hz, 1H), 7.14-7.12 (m, 1H), 6.78-6.74 (m, 3H), 6.59-6.55 (m, 2H), 4.07 (t, J=5.4 Hz, 2H), 3.05 (s, 3H), 2.92-2.88 (m, 2H), 2.69 (bs, 4H), 1.74-1.68 (m, 4H), 1.50 (bs, 2H).

Workup

  1. temperatureto reflux for 1 hour
  2. filtrationFilter the reaction mixture
  3. concentrationconcentrate in vacuo
  4. customPartition the residue between ethyl acetate:methanol (5:1, 6 mL) and saturated aqueous sodium bicarbonate:brine (1:1, 6 mL)
  5. washWash the organic layer with brine
  6. dry with materialdry with sodium sulfate
  7. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-6a82d425915a4a07ae68be9342f5e27c
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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