Ammonium formate → HCID 57500344, compound

HRID 2273527Notes

Reaction equation

HRID 2273527 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([C:18]([O:23]CC4C=CC=CC=4)=[CH:19][CH:20]=[CH:21]3)=[C:16]([O:31][CH3:32])[C:15]=2[CH3:33])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+]>CN(C)C=O.[Pd]>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([C:18]([OH:23])=[CH:19][CH:20]=[CH:21]3)=[C:16]([O:31][CH3:32])[C:15]=2[CH3:33])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57500343HCID 57500343, compound

Product 1

HCID 57500344HCID 57500344, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The mixture of 2.0 g (4.5 mmol) of methyl 2-amino-5-{[8-(benzyloxy)-1-methoxy-2-methylindolizin-3-yl]carbonyl}benzoate and 0.42 g (6.75 mmol) of ammonium formate in the presence of 1.0 g of palladium-on-charcoal (10%) in 20 ml of N,N-dimethylformamide is stirred for 12 hours at ambient temperature under argon. The mixture is filtered under nitrogen and concentrated to dryness so as to obtain 1.51 g of a red oil. The product decomposes on contact with air.

Workup

  1. filtrationThe mixture is filtered under nitrogen
  2. concentrationconcentrated to dryness so as

Sources & evidence

ORD record
ord-4242923b8d0d4f7ab2f9dea6574391c6
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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