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Formic Acid → 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole

HRID 715936
ノート
印刷プレビュー

反応式

HRID 715936 の反応式
[C:1]1([S:7]([NH:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][CH2:22][C:15]4=[CH:14][C:13]=3[C:12]=2C(OC)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].C(O)=O>O1CCOCC1.O.CO>[C:1]1([S:7]([NH:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][CH2:22][C:15]4=[CH:14][C:13]=3[CH:12]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 284Formic AcidHCID 3939Lithium HydroxideHCID 70983444methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2 回

生成物 1

HCID 709841467-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole収率 36.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962
Water
溶媒
2 回
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 26, 0.075 g) and lithium hydroxide mononhydrate (0.049 g) in dioxane (2 mL) and water (1 mL) was irradiated in the microwave at 110° C. for 20 minutes. After cooling, the mixture was diluted with water and acidified to pH4-5 with formic acid. The resultant solid was washed with water and ether, then dried to give a cream powder. The solid was dissolved in methanol and acetone and freeze-dried, then dried in a dessicator, in vacuo, at 40° C. overnight. The solid was triturated with DCM and filtered, washed with DCM (1 mL) and pentane (1 mL) then dried in a dessicator, in vacuo, at 40° C. overnight. The yellow solid was dissolved in hot ethyl acetate and pentane was added until the mixture went cloudy. On cooling, the solid was collected by filtration, washed with pentane and dried in a dessicator, in vacuo, at 40° C. overnight to give 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole (0.023 g) as a cream solid.

後処理

  1. temperatureAfter cooling
  2. washThe resultant solid was washed with water and ether
  3. customdried
  4. customto give a cream powder
  5. dry with materialacetone and freeze-dried
  6. customdried in a dessicator, in vacuo, at 40° C. overnight
  7. customThe solid was triturated with DCM
  8. filtrationfiltered
  9. washwashed with DCM (1 mL) and pentane (1 mL)
  10. customthen dried in a dessicator, in vacuo, at 40° C. overnight
  11. dissolutionThe yellow solid was dissolved in hot ethyl acetate
  12. additionpentane was added until the mixture
  13. temperatureOn cooling
  14. filtrationthe solid was collected by filtration
  15. washwashed with pentane
  16. customdried in a dessicator, in vacuo, at 40° C. overnight

出典と根拠

ORDレコード
ord-f43db273792f4642be99538b3d8de42e
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187494B2

反応ノート

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