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

HRID 36891노트

반응식

HRID 36891 반응식
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

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 19936654HCID 19936654, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-17cb2abf67c74fc7b921c03b909954d2
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418242

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