HCID 22036770, compound → tert-Butyl 6-amino-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 1789972Notes

Reaction equation

HRID 1789972 reaction equation
[N+:1]([C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 22036770HCID 22036770, compound

Product 1

HCID 22036788tert-Butyl 6-amino-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (15.6 g, 49.15 mmol) in ethanol (250 mL) was added a spatula tip of 10% Pd/C. The reaction mixture was shaken under a hydrogen atmosphere (15 psi, Parr apparatus) for 2 h. Upon removal from the Parr apparatus, the reaction mixture was filtered through Celite. The Celite was washed with ethanol and the combined filtrates were concentrated in vacuo to give tert-butyl 6-amino-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate, quantitatively as a white solid: 1H NMR (CDCl3, 500 MHz) δ 1.42–1.67 (m, 9H), 2.74–2.85 (m, 2H), 3.58 (brs, 2H), 3.79 (brs, 2H), 4.60 (brs, 2H), 6.53–6.56 (m, 1H), 6.89–6.99 (m, 2H), 7.77 (brs, 1H) ppm.

Workup

  1. customUpon removal from the Parr apparatus
  2. filtrationthe reaction mixture was filtered through Celite
  3. washThe Celite was washed with ethanol
  4. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-89bcdbe2e2ba44b9afe24a7112355d9b
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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