Sodium Hydroxide → 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylic acid

HRID 62409

反応式

HRID 62409 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([O:18]C)=[O:17])[C:5]2[C:6]([CH3:15])=[CH:7][N:8]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+].CC(OC)(C)C>CO.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=[O:17])[C:5]2[C:6]([CH3:15])=[CH:7][N:8]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:9]=2[CH:10]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 67465536Methyl 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylate

生成物 1

HCID 674653226-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylate (3.24 g, 9.99 mmol) was dissolved in methanol (30 mL) and tetrahydrofuran (THF) (7 mL). The contents were stirred for 5 min., and then aq. 3N NaOH (19.99 mL, 60.0 mmol) was added via addition funnel over 3 min. The contents rapidly became a yellow suspension and were stirred at room temperature for 65 h. The volatiles were removed in vacuo and the residue dissolved in water (60 mL). The contents were washed with ether (1×50 mL). The aq layer was cooled in an ice bath and adjusted to pH 3-4 with 1M HCl, from which an oily residue precipitated. The contents were extracted with EtOAc (2×60 mL). The combined organic layers were dried over magnesium sulfate, filtered through celite, and concentrated in vacuo. The residue obtained was treated with TBME, concentrated in vacuo, and then dried under hi vacuum to afford a yellow foam as 3.08 g (93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70 (t, J=7.33 Hz, 3H), 1.39 (d, J=6.82 Hz, 3H), 1.71-1.86 (m, 2H), 2.30 (s, 3H), 4.48-4.62 (m, 1H), 7.40-7.49 (m, 2H), 7.96 (d, J=1.77 Hz, 1H), 12.99 (s, 1H); LCMS=310.0/312.0 (MH+).

後処理

  1. stirringwere stirred at room temperature for 65 h
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe residue dissolved in water (60 mL)
  4. washThe contents were washed with ether (1×50 mL)
  5. temperatureThe aq layer was cooled in an ice bath
  6. customprecipitated
  7. extractionThe contents were extracted with EtOAc (2×60 mL)
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered through celite
  10. concentrationconcentrated in vacuo
  11. customThe residue obtained
  12. concentrationconcentrated in vacuo
  13. customdried under hi vacuum
  14. customto afford a yellow foam as 3.08 g (93%)

出典と根拠

ORDレコード
ord-15c32c5f7db143baacb8324e262f2aa9
出典データセット
uspto-grants-2016_09
特許番号
US09446041B2

関連ノート

読み込み中…