Ammonium formate → 2,3a,10-trimethyl-6-phenyl-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine

HRID 576535Notes

Reaction equation

HRID 576535 reaction equation
[CH3:1][N:2]1[CH2:11][C:10]2[C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][C:17]=3[N:8]3[C:9]=2[C:4]([CH3:25])([CH2:5][CH:6]=[C:7]3[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][N:2]1[CH2:11][C:10]2[C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][C:17]=3[N:8]3[C:9]=2[C:4]([CH3:25])([CH2:5][CH2:6][CH:7]3[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 533781662,3a,10-trimethyl-6-phenyl-2,3,3a,4-tetrahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine

Product 1

HCID 601683552,3a,10-trimethyl-6-phenyl-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,3a,10-trimethyl-6-phenyl-2,3,3a,4-tetrahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine (100 mg, 0.304 mmol) in MeOH (5 mL) was added 10% Pd—C (100 mg) and ammonium formate (96 mg, 1.524 mmol). The reaction mixture was stirred at 80° C. for 4 h under N2. The reaction mixture was filtered on a Celite bed and washed with MeOH. The filtrate was concentrated under reduced pressure to obtain crude product which was purified by reverse phase HPLC to yield 2,3a,10-trimethyl-6-phenyl-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered on a Celite bed
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto obtain crude product which
  5. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-6d92afe9d14f4b74bc3d2ea0162f172a
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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