Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoate → 4-tert-butyl 7-methyl 1H-indole-4,7-dicarboxylate

HRID 906114ノート

反応式

HRID 906114 の反応式
[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O.[CH:21]([Mg]Br)=[CH2:22]>O1CCCC1>[NH:1]1[C:4]2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:13]=2[CH:22]=[CH:21]1

参加物

4

反応物 2

HCID 23291046Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoateHCID 178418507HCID 178418507、化合物

生成物 1

HCID 674040144-tert-butyl 7-methyl 1H-indole-4,7-dicarboxylate収率 27%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-tert-butyl 1-methyl 2-nitroterephthalate (prepared according to Gao, Y. et. al WO2001070737) (2.15 g, 7.64 mmol) in tetrahydrofuran (30 mL) was added a 1M solution of vinylmagnesium bromide in tetrahydrofuran (23.0 mL) at −40° C., followed by stirring at room temperature for 18 hours. The reaction mixture was quenched by the addition of a solution of 1 M aqueous ammonium chloride, and the organic portion of the solvent was evaporated. The resulting material was partitioned with ethyl acetate (300 mL), and the organic layer was separated then washed with 10% aqueous citric acid (100 mL) and brine, dried over sodium sulfate, filtered and the solvent was concentrated. The resulting crude material was purified by column chromatography (hexane:ethyl acetate 9:1 to 7:3 eluent) to give 4-tert-butyl 7-methyl 1H-indole-4,7-dicarboxylate (0.58 g, 27%). 1H NMR (400 MHz, CDCl3): 10.00 (bs, 1H), 7.88 (dd, 2H), 7.43 (m, 1H), 7.19 (m, 1H), 4.00 (s, 3H), 1.66 (s, 9H). MS (EI) for C15H17NO4: 274 (M−H).

後処理

  1. customThe reaction mixture was quenched by the addition of a solution of 1 M aqueous ammonium chloride
  2. customthe organic portion of the solvent was evaporated
  3. customThe resulting material was partitioned with ethyl acetate (300 mL)
  4. customthe organic layer was separated
  5. washthen washed with 10% aqueous citric acid (100 mL) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe solvent was concentrated
  9. customThe resulting crude material was purified by column chromatography (hexane:ethyl acetate 9:1 to 7:3 eluent)

出典と根拠

ORDレコード
ord-60b442cc47364669b2a300eb240a9895
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

読み込み中…