Methanol → HCID 68254813, compound

HRID 1668499Notes

Reaction equation

HRID 1668499 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-])=O)=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[CH:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].O.NN.[CH3:31]O>[Ni]>[NH2:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16]([C:13]3[CH2:14][CH2:15][CH:10]([N:2]([CH2:1][CH3:31])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:11][CH:12]=3)=[CH:17][NH:18]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 59004649tert-Butyl methyl(4-(6-nitro-1H-indol-3-yl)cyclohex-3-enyl)carbamate

Product 1

HCID 68254813HCID 68254813, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of compound 127 (0.2 g, 0.518 mmol) in dry MeOH (3 mL) was treated with Ra—Ni (0.02 g) followed by hydrazine hydrate (0.16 mL, 5.188 mmol) at room temperature. The reaction was placed in a pre-heated oil bath and refluxed for 2 min. The reaction brought to room temperature, filtered through celite bed and washed with methanol (2×15 mL). The solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain compound 130 as a foam. 1H NMR (DMSO-d6) δ 1.08 (t, 3H, J=6.9 Hz), 1.41 (s, 9H), 1.72-1.89 (m, 2H), 2.18-2.60 (m, 4H), 3.10-3.20 (m, 2H), 4.01 (brs, 1H), 4.71 (s, 2H), 6.02 (brs, 1H), 6.39 (dd, 1H, J=1.5, 8.5 Hz), 6.51 (d, 1H, J=1.8 Hz), 6.99 (d, 1H, J=2.1 Hz), 7.43 (d, 1H, J=8.4 Hz), 10.44 (s, 1H); ESI-MS (m/z, %): 378 (M+Na, 8), 356 (MH+,4), 300 (100).

Workup

  1. customThe reaction was placed in a pre-heated oil bath
  2. temperaturerefluxed for 2 min
  3. custombrought to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with methanol (2×15 mL)
  6. customThe solvent was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 2.5:97.5)

Sources & evidence

ORD record
ord-1e998cc7cec741d288b04378a7306c6d
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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