Sodium hydride → 2,6-Difluorobenzenesulfonic acid 7-methyl-1-phenethyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester hydrochloride

HRID 1766273Notes

Reaction equation

HRID 1766273 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:26])[CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:8]=[C:7]2[CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1.[H-].[Na+].[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=1[S:37]([Cl:40])(=[O:39])=[O:38]>C1COCC1>[ClH:40].[CH3:1][C:2]1[CH:3]=[C:4]([O:26][S:37]([C:31]2[C:32]([F:36])=[CH:33][CH:34]=[CH:35][C:30]=2[F:29])(=[O:39])=[O:38])[CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:8]=[C:7]2[CH:19]1[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 694335207-Methyl-3-(1-methylpiperdin-4-yl)-1-phenethyl-1H-indol-5-ol

Product 1

HCID 878266472,6-Difluorobenzenesulfonic acid 7-methyl-1-phenethyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester hydrochlorideYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 56, using 7-methyl-3-(1-methylpiperdin-4-yl)-1-phenethyl-1H-indol-5-ol (0.55 mmol, 0.190 g) in THF (1.4 mL), sodium hydride (0.65 mmol, 0.026 g, 60% dispersion in mineral oil), and 2,6-diflurobenzenesulfonyl chloride (0.60 mmol, 0.128 g) afforded 0.136 g (44%) of the title compound: MS (ion spray): m/z=511 (M+1); 1H NMR (DMSOd6): 7.97-7.87 (m, 1H), 7.45-7.38 (m, 2H), 7.29-7.17 (m, 2H), 7.13 (d, 2H), 6.63 (d, J=1.10 Hz, 1H), 4.53 (t, J=7.50 Hz, 2H), 3.47-3.39 (m, 2H), 3.11-2.95 (m, 4H), 2.87-2.69 (m, 4H), 2.60 (s, 3H), 1.94-1.71 (mm, 4H); Calculated for C28H28F2N2O3S-1.9 H2O: C, 61.73; H, 5.88; N, 5.14. Found: C, 61.43; H, 5.51; N, 4.93.

Sources & evidence

ORD record
ord-885313c9b0de4fca882dc6e49bde4ba1
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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