1-Bromopropane → 1-Propyl-1H-indole-2,5-dicarboxylic acid

HRID 1829983ノート

反応式

HRID 1829983 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=[O:16].[CH2:18](Br)[CH2:19][CH3:20]>CN(C=O)C>[CH2:18]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=[O:16])[CH2:19][CH3:20]

参加物

5

反応物 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 43083261H-indole-2,5-dicarboxylic Acid

生成物 1

HCID 220564451-Propyl-1H-indole-2,5-dicarboxylic acid収率 68.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% suspension, 125 mg, 5 mmol) was added to a stirred solution of 1H-indole-2,5-dicarboxylic acid (525 mg, 2 mmol) in dry DMF (10 mL) and maintained at ambient temperature for 1 hour. The reaction was cooled to 0° C. and then propyl bromide (0.275 mL, 3 mmol) was added. After 3 days the reaction was quenched by addition of 5% aqueous NH4Cl. The mixture was concentrated to dryness and then purified on a silica gel column using 5% EtOAc/toluene. The product was then dissolved in 30 mL ethanol and 10 mL of 2 M NaOH was added. The solution was heated at 55° C. for 2 days. The ethanol was removed in vacuo and the resulting aqueous solution was acidified with 0.01 M HCl to pH 3. The resulting precipitate was filtered and rinsed twice with water. The isolated product was dried by evaporation from absolute ethanol (3×) to give 340 mg (67%) of 87.

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. customAfter 3 days the reaction was quenched by addition of 5% aqueous NH4Cl
  3. concentrationThe mixture was concentrated to dryness
  4. custompurified on a silica gel column
  5. dissolutionThe product was then dissolved in 30 mL ethanol
  6. addition10 mL of 2 M NaOH was added
  7. temperatureThe solution was heated at 55° C. for 2 days
  8. customThe ethanol was removed in vacuo
  9. filtrationThe resulting precipitate was filtered
  10. washrinsed twice with water
  11. dry with materialThe isolated product was dried by evaporation from absolute ethanol (3×)

出典と根拠

ORDレコード
ord-8d0c443e5c114adc9fb6b053cd42f889
出典データセット
uspto-grants-2006_06
特許番号
US07064218B2

反応ノート

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