Ammonium formate → HCID 68283817, compound

HRID 1469495Notes

Reaction equation

HRID 1469495 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]#[C:12][N:13]3[C:21]4[CH:20]=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[C:15]4[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:14]3=4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:27][N:24]1[CH2:25][CH2:26][C:14]2[N:13]([CH2:12][CH2:11][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH2:4][CH2:3][NH:2][CH2:1]4)[C:21]3[CH:20]=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[C:15]=2[CH2:23]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68283925HCID 68283925, compound

Product 1

HCID 68283817HCID 68283817, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-isoquinolin-5-ylethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (80 mg, 0.228 mmol) in MeOH (5 mL) were added 10% dry Pd—C (80 mg) and ammonium formate (72 mg, 1.14 mmol). The reaction mixture was refluxed for 4 h and filtered through Celite. The filtrate was concentrated under reduced pressure to afford crude product, which was purified by reverse phase HPLC to yield 20 mg of 2,8-dimethyl-5-[2-(1,2,3,4-tetrahydro-isoquinolin-5-yl)-ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.21 (d, 1H), 7.18 (m, 2H), 7.1 (d, 1H), 7.0 (d, 1H), 6.93 (d, 1H), 4.7 (d, 1H), 4.2-4.4 (m, 5H), 3.7 (m, 1H), 3.2 (m, 3H), 3.08 (t, 2H), 3.02 (s, 3H), 2.83 (m, 1H), 2.6-2.8 (m, 3H), 2.4 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford crude product, which
  5. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-dbb8ad7adc194b578b14aba336533304
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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