3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → HCID 10137156, compound

HRID 1766259Notes

Reaction equation

HRID 1766259 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.[OH-].[Na+]>>[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][S:10]([C:3]4[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=4[F:1])(=[O:12])=[O:11])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 14798Sodium HydroxideHCID 27769772,3,4-Trifluorobenzenesulfonyl chloride

Product 1

HCID 10137156HCID 10137156, compoundYield 105.8%

Procedure

By a method similar to Example 31, using 2,3,4-trifluorobenzenesulfonyl chloride (280 mg, 1.2 mmol) and 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (231 mg, 1.0 mmol) and 0.2 N sodium hydroxide (5.5 mL, 1.1 mmol) gave 449 mg of a purple foam. The crude product was purified by radial chromatography (silica gel, 2000 micron rotor, 100/10 methylene chloride/methanol then 100/10/0.5 methylene chloride/methanol/ammonium hydroxide) to give 418 mg (98%) of homogeneous product. The product was crystallized from ethyl acetate/hexanes to give 280 mg of the title compound as a white powder: mp=160-162° C.; MS(m/e): 424 (M+); Calculated for C20H19F3N2O3S: C, 56.60; H, 4.51; N, 6.60. Found: C, 56.53; H, 4.78; N, 6.51.

Sources & evidence

ORD record
ord-721751c6a6a9492b8eafcab89a5e8cde
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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