Triethylamine → 3-Formyl-2-methyl-8-(2-(trans)-methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine

HRID 1195743ノート

反応式

HRID 1195743 の反応式
C(N(CC)CC)C.[CH:8]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][C@H:21]3[OH:29])[C:13]2=[N:12][C:11]=1[CH3:30])=[O:9].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH:8]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][C@H:21]3[O:29][S:32]([CH3:31])(=[O:34])=[O:33])[C:13]2=[N:12][C:11]=1[CH3:30])=[O:9]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 228438253-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

生成物 1

HCID 228438343-Formyl-2-methyl-8-(2-(trans)-methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

8.5 ml triethylamine is added, while stirring and excluding any moisture, to 10 g 3-formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine, suspended in 200 ml dry dichloromethane. This is cooled in an icebath and 5 ml methane sulfonyl chloride dissolved in 10 ml dry dichloromethane is added dropwise. This is stirred for 1 hour while cooling with ice, and the solution is poured onto icewater and extracted several times with dichloromethane. The organic phases are washed with water and dried, and the solvent is stripped off in vacuo. The yellowish residue is stirred with diethyl ether, filtered off under suction and dried. 12 g of the title compound of m.p. 158°-160° C. is obtained. By analogous methods 2-methyl-8-(2-(trans)methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine is obtained from 2-methyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine and methane sulfonyl chloride. M.p. 122°-125° C. (decomposition).

後処理

  1. additionis added dropwise
  2. stirringThis is stirred for 1 hour
  3. temperaturewhile cooling with ice
  4. additionthe solution is poured onto icewater
  5. extractionextracted several times with dichloromethane
  6. washThe organic phases are washed with water
  7. customdried
  8. stirringThe yellowish residue is stirred with diethyl ether
  9. filtrationfiltered off under suction
  10. customdried

出典と根拠

ORDレコード
ord-cce343358ad24aa694f8333ac01fb7b1
出典データセット
uspto-grants-1992_05
特許番号
US05112834

反応ノート

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