Ammonium formate → HCID 68283756, compound

HRID 1630554Notes

Reaction equation

HRID 1630554 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]>[CH:1]1[C:10]2[C:5](=[C:6]([CH:11]=[CH: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

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68283925HCID 68283925, compound

Product 1

HCID 68283756HCID 68283756, compoundYield 22.1%

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 (90 mg, 0.256 mmol) in MeOH (6 mL) were added 10% dry Pd—C (25 mg) and ammonium formate (81 mg, 1.282 mmol). The reaction mixture was refluxed for 2 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 5-(2-isoquinolin-5-yl-vinyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CD3OD, TFA salt) δ (ppm): 9.7 (s, 1H), 8.57 (d, 1H), 8.5 (d, 1H), 8.3 (d, 1H), 7.65 (t, 1H), 7.59 (d, 1H), 7.4 (d, 1H), 7.22 (d, 1H), 7.2 (s, 1H), 6.7 (m, 2H), 4.63 (d, 1H), 4.3 (d, 1H), 3.7 (m, 1H), 3.47 (m, 1H), 3.08 (s, 3H), 2.9-3.0 (m, 2H), 2.31 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 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-5d05774f9ce34a2ebfe73109026e2ba1
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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