HCID 59129406, compound → HCID 59129333, compound

HRID 1847782Notes

Reaction equation

HRID 1847782 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[CH:6]=[C:5]1[C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][OH:19]>[Ni].CO>[NH2:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:4]([CH2:3][CH2:2][OH:1])[C:5]([C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][OH:19])=[CH:6]2

Participants

4

Reactant 1

HCID 59129406HCID 59129406, compound

Product 1

HCID 59129333HCID 59129333, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[1-(2-hydroxy-ethyl)-5-nitro-1H-indol-2-yl]-3-methyl-butan-1-ol (300 mg, 1.03 mmol) and Raney Nickel (200 mg) in CH3OH (30 mL) was stirred for 5 h at room temperature under a H2 atmosphere. The catalyst was filtered through a celite pad and the filtrate was evaporated under vacuum to give a residue, which was purified by preparative TLC to afford 3-[5-amino-1-(2-hydroxy-ethyl)-1H-indol-2-yl]-3-methyl-butan-1-ol (70 mg, 26%). 1H NMR (300 MHz, CDCl3) δ 7.07 (d, J=8.7 Hz, 1H), 6.83 (d, J=2.1 Hz, 1H), 6.62 (dd, J=2.1, 8.4 Hz, 1H), 6.15 (s, 1H), 4.47 (t, J=5.4 Hz, 2H), 4.07 (t, J=5.4 Hz, 2H), 3.68 (t, J=5.7 Hz, 2H), 2.16 (t, J=5.7 Hz, 2H), 4.00-3.91 (m, 4H), 2.76 (s, 2H), 1.61 (s, 6H), 1.42 (s, 6H).

Workup

  1. filtrationThe catalyst was filtered through a celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customto give a residue, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-db9c9843af12461faf20386930d8632b
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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