Lithium Chloride → tert-Butyl-4-((5-cyanobenzo[d]oxazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174075ノート

反応式

HRID 2174075 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li+].[Cl-].[CH:14]([C:16]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]2[C:17]=1[CH:18]=[CH:19][N:20]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:15]>C1COCC1.[NH4+].[Cl-].[Cl-].[Na+].O>[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][C:2]([CH:14]([OH:15])[C:16]3[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]4[C:17]=3[CH:18]=[CH:19][N:20]4[C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])=[N:3][C:4]=2[CH:9]=1)#[N:11]

参加物

7

反応物 3

HCID 433294Lithium ChlorideHCID 203806861,3-Benzoxazole-5-carbonitrileHCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701709tert-Butyl-4-((5-cyanobenzo[d]oxazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of benzo[d]oxazole-5-carbonitrile (CAS #:132227-01-1) (0.996 g, 6.91 mmol) in THF (20 mL), TMPMgCl.LiCl (1 M in THF) (6.91 mL, 6.91 mmol) was added at −78° C. After stirring for 30 min, tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (1.00 g, 3.46 mmol) was added at −78° C. Then, the reaction mixture was warmed to rt. After stirring for 10 min, the reaction was heated at 50° C. After stirring for 1.5 h, the reaction mixture was cooled to rt, and diluted with aq. NH4Cl and brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with a 1:1 solution of 1M aq. NaHSO4 and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60) to give the title compound. MS (ESI) m/z 432.3 (MH).

後処理

  1. stirringAfter stirring for 10 min
  2. temperaturethe reaction was heated at 50° C
  3. stirringAfter stirring for 1.5 h
  4. temperaturethe reaction mixture was cooled to rt
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organic layers were washed with a 1:1 solution of 1M aq. NaHSO4 and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60)

出典と根拠

ORDレコード
ord-b68b35316b9846bf89cc9d3b6033f441
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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