1-Propanol → 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-, propyl ester

HRID 217955ノート

反応式

HRID 217955 の反応式
[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:8]2[C:7]([C:17]#N)=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=[O:26])=CC=1.[CH2:30]([OH:33])[CH2:31][CH3:32]>COC(C)(C)C>[CH2:30]([O:33][C:17]([C:7]1[C:8]2[C:9](=[N:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=1)=[O:26])[CH2:31][CH3:32]

参加物

5

反応物 3

HCID 10311-PropanolHCID 6101p-Toluenesulfonic acidHCID 669245201H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(1,1-dimethylethyl)-5-nitro-

生成物 1

HCID 669245181H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-, propyl ester収率 88%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

To a suspension of 5.0 g (20.47 mmol) of 1-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile in 125 mL of n-propanol, 7.78 g of p-toluensulfonic acid were added under stirring. The mixture was heated at reflux for 40 hours and then it was cooled to room temperature and diluted with 70 mL of tert-butyl methyl ether. The precipitate was filtered off and the clear filtrate was concentrated under vacuum to a small volume (about 40-50 mL). The suspension was cooled to −5/0° C. and kept at this temperature for 2 hours. The solid was filtered, washed with 20 mL of 1:1 mixture of n-propanol and tert-butyl methyl ether and dried to afford 5.50 g of the title compound as a cream-colored solid.

後処理

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 40 hours
  4. filtrationThe precipitate was filtered off
  5. concentrationthe clear filtrate was concentrated under vacuum to a small volume (about 40-50 mL)
  6. temperatureThe suspension was cooled to −5/0° C.
  7. filtrationThe solid was filtered
  8. washwashed with 20 mL of 1:1 mixture of n-propanol and tert-butyl methyl ether
  9. customdried

出典と根拠

ORDレコード
ord-668c62337f25451aae9f96859c6d4982
出典データセット
uspto-grants-2012_06
特許番号
US08198298B2

反応ノート

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