Benzenesulfonyl chloride → HCID 10179007, compound

HRID 1766274Notes

Reaction equation

HRID 1766274 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:12])=[CH:8][C:9]=2[CH3:11])[C:4]([CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:3]1.[H-].[Na+].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:12][S:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:30])=[O:29])=[CH:8][C:9]=2[CH3:11])[C:4]([CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:3]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 69431066HCID 69431066, compound

Product 1

HCID 10179007HCID 10179007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 56, using 1,7-dimethyl-3-(1-methylpiperdin-4-yl)-5-hydroxy-1H-indol (1.98 mmol, 0.511 g) in THF (5.0 mL), sodium hydride (2.37 mmol, 0.095 g, 60% dispersion in mineral oil), and benzenesulfonyl chloride (2.18 mmol, 0.384 g), afforded 0.501 g (64%): ms (ion spray): m/z=399 (M+1); 1H NMR (DMSOd6): 7.85-7.77 (m, 3H), 7.67-7.62 (m, 2H), 7.01 (s, 1H), 6.64 (d, J=2.56 Hz, 1H), 6.55 (d, J=1.83 Hz, 1H), 3.94 (s, 3H), 2.82-2.72 (bd, 2H), 2.60 (s, 3H), 2.39 (tt, J=3.72 Hz, 1H), 2.18 (s, 3H), 1.91 (m, 2H), 1.67-1.54 (m, 2H), 1.47 (m, 2H); Calculated for C22H26N2O3S: C, 66.31; H, 6.58; N, 7.03. Found: C, 66.18; H, 6.58; N, 7.08.

Workup

  1. customafforded 0.501 g (64%)

Sources & evidence

ORD record
ord-66bc2230f8b4437fa0aa7a24f2872ca5
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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