Ammonium formate → HCID 25232990, compound

HRID 1469453Notes

Reaction equation

HRID 1469453 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:11]2=3)[CH:5]=[N:6][CH:7]=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:11]2=3)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68283644HCID 68283644, compound

Product 1

HCID 25232990HCID 25232990, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a degassed solution of 5-(5-fluoro-pyridin-3-ylethynyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (60 mg, 0.188 mmol) in MeOH (3 mL) were added 10% dry Pd—C (35 mg) and ammonium formate (59 mg, 0.940 mmol). The reaction mixture was stirred at 75° C. for 1 h. The reaction mass was filtered through Celite and the filtrate concentrated under reduced pressure to afford crude product, which was purified by reverse phase HPLC to yield 5-[2-(5-fluoro-pyridin-3-yl)-ethyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.3 (s, 1H), 7.9 (s, 1H), 7.38 (d, 1H), 7.21 (s, 1H), 7.2 (d, 1H), 7.0 (d, 1H), 4.62 (d, 1H), 4.4 (t, 2H), 4.3 (d, 1H), 3.78 (m, 1H), 3.4 (m, 1H), 3.18 (t, 2H), 3.1 (s, 3H), 2.9 (m, 1H), 2.8 (m, 1H), 2.4 (s, 3H).

Workup

  1. filtrationThe reaction mass was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto afford crude product, which
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d20c4eceae0f4b6fab1e69ca9a6fc1c2
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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