Cesium carbonate → N-(4-bromobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

HRID 1011548Notes

Reaction equation

HRID 1011548 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:17][CH:16]3[CH:18]([OH:19])[CH:13]2[CH2:14][CH2:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1.ClC1C=CC(S(N(CC2C=CC(C#N)=CC=2)[C@@H]2CCC[C@H]2CO)(=O)=O)=CC=1>>[Br:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:11]([CH:12]2[CH2:17][CH:16]3[CH:18]([OH:19])[CH:13]2[CH2:14][CH2:15]3)[S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 685274-Bromobenzyl bromideHCID 59497772HCID 59497772, compoundHCID 594977942-(4-Chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol

Product 1

HCID 59497797N-(4-bromobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamideYield 72.4%

Procedure

The title compound was synthesized from 2-(4-chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol (302 mg, 1.0 mmol), cesium carbonate (652 mg, 2.0 mmol), and 1-bromo-4-(bromomethyl)benzene (300 mg, 1.2 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 2) to give N-(4-bromobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (341 mg, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 7.65-7.72 (2H, m), 7.40-7.46 (2H, m), 7.37 (2H, d, J=8.56 Hz), 7.18 (2H, d, J=8.56 Hz), 4.68 (2H, dd, J=38.27, 17.12 Hz), 3.97 (1H, t, J=7.30 Hz), 3.77 (1H, s), 1.94 (1H, hr. s.), 1.79-1.88 (3H, m), 1.36-1.62 (3H, m), 1.00-1.12 (2H, m). LC/MS R.T.=2.33 min; [M+H]+=470.03. HRMS [M+H]+ calc'd 470.0192, found 470.0202.

Sources & evidence

ORD record
ord-8de65b033f544d7a9a6a666b5c3cccaa
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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