Methanol → HCID 68254813、化合物

HRID 1668499ノート

反応式

HRID 1668499 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 68254813HCID 68254813、化合物

試薬・触媒・溶媒 1

HCID 935Nickel触媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1e998cc7cec741d288b04378a7306c6d
出典データセット
uspto-grants-2011_08
特許番号
US07989447B2

反応ノート

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