Ammonia → 3-[(1-methylpiperidin-4-yl)thio]-1H-indol-5-ol

HRID 36891ノート

反応式

HRID 36891 の反応式
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[S:16][CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1.N>C(Cl)(Cl)Cl>[CH3:23][N:20]1[CH2:19][CH2:18][CH:17]([S:16][C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([OH:6])[CH:8]=3)[NH:12][CH:11]=2)[CH2:22][CH2:21]1

参加物

5

反応物 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 19936654HCID 19936654、化合物

生成物 1

HCID 199366023-[(1-methylpiperidin-4-yl)thio]-1H-indol-5-ol収率 10.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A solution of boron tribromide (6.3 ml) in chloroform (16 ml) is added dropwise to a solution of 5-methoxy-3-[(1-methylpiperidin-4-yl)thio]-1H-indole (8 g, prepared in Example 41) in chloroform (105 ml) at 0° C. After 3 hours at room temperature, the reaction mixture is poured onto ice and rendered basic with aqueous ammonia. The organic phase is dried over sodium sulfate and concentrated. The oily residue is chromatographed on silica gel (eluent: CH2Cl2 /EtOH/iPrNH2 79/20/1) to give 3-[(1-methylpiperidin-4-yl)thio]-1H-indol-5-ol (0.8 g), which is recrystallized from xylene.

後処理

  1. additionthe reaction mixture is poured onto ice
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe oily residue is chromatographed on silica gel (eluent: CH2Cl2 /EtOH/iPrNH2 79/20/1)

出典と根拠

ORDレコード
ord-17cb2abf67c74fc7b921c03b909954d2
出典データセット
uspto-grants-1995_05
特許番号
US05418242

反応ノート

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