Ammonium formate → HCID 53373421, compound

HRID 1499086Notes

Reaction equation

HRID 1499086 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([N:11]3[C:19]4[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=4[C:13]4[CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:12]3=4)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH:26]([O-])=[O:27].[NH4+]>CO.[Pd]>[CH3:25][N:22]1[CH2:23][CH2:24][C:12]2[N:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[CH2:1][N:2]([CH:26]=[O:27])[CH2:3][CH2:4]4)[C:19]3[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[C:13]=2[CH2:21]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67379371HCID 67379371, compound

Product 1

HCID 53373421HCID 53373421, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a de-aerated solution of 5-isoquinolin-6-yl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (35 mg, 0.10 mmol) in MeOH (5 mL) were added 10% Pd—C (18 mg) and ammonium formate (68 mg, 1.07 mmol). The reaction mixture was refluxed for 15 h and filtered through Celite. The filtrate was concentrated under reduced pressure to afford crude material, which was purified by column chromatography using silica (100:200) and 3% MeOH-DCM to yield 6-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-3,4-dihydro-1H-isoquinoline-2-carbaldehyde (10 mg). 1H NMR (HCl salt, CD3OD) δ (ppm): 8.2 (s, 1H), 7.41 (s, 1H), 7.3 (s, 1H), 7.25 (m, 2H), 7.1 (d, 1H), 7.03 (d, 1H), 4.7 (d, 1H), 4.4 (d, 1H), 3.8 (m, 3H), 3.57 (m, 3H), 3.17 (s, 3H), 3.0 (m, 4H), 2.4 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford crude material, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cd603b6dd94b4715b2bd732269389f69
Source dataset
uspto-grants-2015_12
Patent number
US09199985B2

Reaction notes

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