Diisopropyl Ether → HCID 57500356, compound

HRID 2273534Notes

Reaction equation

HRID 2273534 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([CH:18]=[CH:19][C:20]([O:23]CC4C=CC=CC=4)=[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+].C(OC(C)C)(C)C>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]([CH:18]=[CH:19][C:20]([OH:23])=[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

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 2723923Ammonium formateHCID 57500355HCID 57500355, compound

Product 1

HCID 57500356HCID 57500356, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The mixture of 0.95 g (2.14 mmol) of methyl 2-amino-5-[(6-benzyloxy-1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate, 0.21 g (3.21 mmol) of ammonium formate and 0.19 g of palladium-on-charcoal at 10% in 12 ml of N,N-dimethylformamide is stirred for 4 hours at ambient temperature. It is then filtered and concentrated to dryness. The solid obtained is taken up with diisopropyl ether and then filtered, to give 0.64 g (85%) of a yellow powder.

Workup

  1. filtrationIt is then filtered
  2. concentrationconcentrated to dryness
  3. customThe solid obtained
  4. filtrationfiltered

Sources & evidence

ORD record
ord-dfe5556dcd5d4f9390a3f1788007ad04
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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