O,O-Dipyridin-2-yl carbonothioate → 1-t-Butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole

HRID 1275651ノート

反応式

HRID 1275651 の反応式
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.C1C=C(O[C:26](OC2N=CC=CC=2)=[S:27])N=CC=1>C(Cl)Cl>[C:15]([O:14][C:12]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([N:1]=[C:26]=[S:27])[C:10]=2[CH3:11])[CH2:6][CH2:7]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

参加物

4

反応物 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 158963716-Amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole

生成物 1

HCID 158963721-t-Butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole収率 95.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

6-Amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole (0.5 g, 2.13 mmol) is dissolved in methylene chloride (10 mL). To this solution is added N,N-dimethylaminopyridine (0.052 g, 0.42 mmol) and di-2-pyridyl thionocarbonate (0.496 g, 2.13 mmol). The solution is allowed to stir for 20 minutes. The solution is diluted with methylene chloride and washed first with four 75-mL portions of aqueous citric acid solution followed by three 100-mL portions of aqueous potassium carbonate. The organic extracts are dried over anhydrous potassium carbonate, filtered and the solvent is removed by rotary evaporation to yield 0.59 g of crude 1-t-butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole as an orange, oily solid. The crude product is taken on to the next reaction without further purification.

後処理

  1. washwashed first with four 75-mL portions of aqueous citric acid solution
  2. dry with materialThe organic extracts are dried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customthe solvent is removed by rotary evaporation

出典と根拠

ORDレコード
ord-536f35938d5e44fc9b71fcb4fb929573
出典データセット
uspto-grants-2000_12
特許番号
US06162818

反応ノート

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