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

HRID 36891Notes

Reaction equation

HRID 36891 reaction equation
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

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 19936654HCID 19936654, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-17cb2abf67c74fc7b921c03b909954d2
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

Loading…