Ammonium formate → HCID 46235887, compound

HRID 333170Notes

Reaction equation

HRID 333170 reaction equation
N1C=[CH:5][C:4]([CH:7]=[C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=4)[CH:15]=3)[NH:10][C:9]2=[O:29])=[CH:3][CH:2]=1.[CH:30]([O-])=O.[NH4+:33]>CO.[Pd]>[N:33]1[CH:30]=[CH:2][CH:3]=[C:4]([CH2:7][CH:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=4)[CH:15]=3)[NH:10][C:9]2=[O:29])[CH:5]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66778493HCID 66778493, compound

Product 1

HCID 46235887HCID 46235887, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-pyridin-4-ylmethylene-5-(3,4,5-trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (50 mg, 0.128 mmol) in MeOH (4 ml) was added ammonium formate (245 mg, 3.85 mmol) and Pd/C (10%, 30 mg). The mixture was stirred at room temperature for 3 hrs after which it was filtered, evaporated, and partitioned between water and DCM. The title compound (33 mg, 66%) was obtained after silica gel chromatography eluting with 0-10% MeOH:DCM. 1H NMR (CDCl3, 300 MHz): δ 10.05 (s, 1H), 8.60 (d, J=2.6 Hz, 1H), 8.45 (d, J=1.1 Hz, 1H), 8.38 (d, J=1.2 Hz, 1H), 7.62 (d, J=4.7 Hz, 1H), 7.35 (dd, J=2.9, 4.7 Hz, 1H), 6.53 (d, J=1.2 Hz, 1H), 6.38 (s, 1H), 3.95 (m, 1H), 3.90 (m, 1H), 3.85 (s, 6H), 3.84 (s, 3H), 3.84 (m, 1H).

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. custompartitioned between water and DCM

Sources & evidence

ORD record
ord-c0ce0dfc620b4909a2d6b8644299d252
Source dataset
uspto-grants-2014_11
Patent number
US08877772B2

Reaction notes

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