Triphenylphosphine Oxide → 7-(Benzyloxy)-2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole

HRID 1851458ノート

反応式

HRID 1851458 の反応式
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:36]([O:43][C:44]1[CH:45]=[CH:46][CH:47]=[C:48]2[C:52]=1[NH:51][C:50]([C:53]([NH:55][CH2:56][CH2:57][S:58]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:49]2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[CH2:36]([O:43][C:44]1[CH:45]=[CH:46][CH:47]=[C:48]2[C:52]=1[NH:51][C:50]([C:53]1[S:58][CH2:57][CH2:56][N:55]=1)=[CH:49]2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

5

反応物 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 579018537-(Benzyloxy)-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

生成物 1

HCID 579016087-(Benzyloxy)-2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole収率 27%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of triphenylphosphine oxide (4.70 g) in dichloromethane (20 mL) was slowly added trifluoromethanesulfonic anhydride (1.42 mL) at 0° C. The mixture was stirred for 10 min, and 7-(benzyloxy)-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (1.60 g) was added. The reaction mixture was stirred at room temperature for 3 hr and concentrated. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.23 g, yield 27%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:20→1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 129-130° C.

後処理

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 3 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c3c5b5ad290f4e00a2fce1303f82b0f3
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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