3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → 4-Iodobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester

HRID 1766254Notes

Reaction equation

HRID 1766254 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([OH:28])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>C1COCC1>[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][S:8]([C:5]4[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=4)(=[O:10])=[O:9])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 73994-Iodobenzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 103003764-Iodobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl esterYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

By a method similar to Example 31, using 4-Iodobenzenesulfonyl chloride (347 mg, 1.15 mmol) in THF (4 mL), 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (220 mg, 0.96 mmol) in 0.2 N sodium hydroxide (5.2 mL, 1.05 mmol) and THF (4 mL) gave 470 mg of an off white solid. The crude product was recrystallized from ethyl acetate/hexanes to give 404 mg (85%) of tan crystals: mp=174-176° C.; MS(m/e): 495 (M−1); Calculated for C20H21N2O3S: Calcd: C, 48.40; H, 4.26; N, 5.64. Found: C, 48.74; H, 4.20; N, 5.59.

Workup

  1. customThe crude product was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7de624c923c846cbacaf77bec07a9a57
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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