Ethanol → N-methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

HRID 2093342Notes

Reaction equation

HRID 2093342 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]([CH3:25])[C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[NH:22][CH:23]=[CH:24][C:17]=23)[CH2:9]1)C1C=CC=CC=1.C(O)C>Cl.O.[Pd]>[CH3:25][N:15]([C@@H:10]1[C@H:11]([CH3:14])[CH2:12][CH2:13][NH:8][CH2:9]1)[C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[NH:22][CH:23]=[CH:24][C:17]=12

Participants

6

Reactant 2

HCID 702EthanolHCID 66663007N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

Product 1

HCID 66662875N-methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amineYield 236.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A degassed mixture of N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine (0.030 g, 0.000090 mol) and palladium (0.028 g, 0.000026 mol) in ethanol (2 mL, 0.03 mol) and 3.0 M of hydrogen chloride in water (0.2 mL) was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered and washed with MeOH. The solvent was removed under vacuum to give 52 mg of an orange viscous oil. The oil was partitioned between ethyl acetate and sat. NaHCO3. The aqueous phase was extracted with ethyl acetate and THF. The combined organic phases were washed with sat. NaCl. Solvents were removed under vacuum to give 47 mg of an orange solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with MeOH
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0908c809eeac4cfba80e2447f81502c2
Source dataset
uspto-grants-2013_05
Patent number
US08445488B2

Reaction notes

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