Ammonium formate → HCID 57675753, compound

HRID 2264708Notes

Reaction equation

HRID 2264708 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:26][O:27][CH3:28])=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[CH3:25][O:24][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[N:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[C:16]([CH2:26][O:27][CH3:28])=[CH:17]2

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 57675751HCID 57675751, compound

Product 1

HCID 57675753HCID 57675753, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Benzyloxyphenyl)-5-methoxy-2-methoxymethyl-1H-indole (0.16 g, 0.43 mmol) was dissolved in methanol (3 mL) and tetrahydrofuran (1 mL). Palladium on carbon (0.32 g, 10% wet) and ammonium formate (0.14 g, 2.14 mmol) were added, and the reaction was stirred at reflux for 2 hours. The mixture was cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated, and the crude material taken on without purification. LC-MS (C17H17NO3 calc'd 283) m/z 284 (M+H).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. customthe crude material taken on without purification

Sources & evidence

ORD record
ord-17c13416ed2a45f495537f463b5278eb
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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