Acetonitrile → 8-(Methylsulfonylamino)quinoline

HRID 336117Notes

Reaction equation

HRID 336117 reaction equation
N1C2C(=CC=CC=2[CH2:11][S:12]([NH2:15])(=[O:14])=[O:13])C=CC=1.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].[CH3:39][C:40]#[N:41]>>[N:41]1[C:19]2[C:18](=[CH:23][CH:22]=[CH:21][C:20]=2[NH:15][S:12]([CH3:11])(=[O:14])=[O:13])[CH:17]=[CH:39][CH:40]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 43164318quinolin-8-ylmethanesulfonamide

Product 1

HCID 1515068-(Methylsulfonylamino)quinolineYield 63%

Procedure

N-(quinolin-8-yl)methanesulfonamide was synthesized as previously described. 2N-(quinolin-8-yl)methanesulfonamide (0.08 g, 0.34 mmol), was reacted with 4-bromomethylphenyl boronic acid pinacol ester (0.11 g, 0.37 mmol), in the presence of K2CO3 (0.14 g, 1.0 mmol) in 3 mL MeCN in a microwave reactor at 90° C. for 30 min affording B15 in 63% yield (0.09 g, 0.21 mmol). 1H NMR (400 MHz, CDCl3) δ=8.97 (dd, J1=4 Hz, J2=1.6 Hz, 1H), 8.18 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.74 (dd, J1=8.4 Hz, J2=1.2 Hz, 1H), 7.64 (d, J=8 Hz, 2H), 7.50 (dd, J1=7.2 Hz, J2=1.2 Hz, 1H), 7.46 (dd, J1=8.4 Hz, J2=4.4 Hz, 1H), 7.36 (t, J=7.6 Hz, 1H), 7.22 (d, J=8 Hz, 2H), 5.20 (s, 2H), 3.20 (s, 3H), 1.30 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=150.30, 145.18, 140.39, 137.00, 135.36, 135.17, 134.93, 129.74, 129.06, 128.25, 126.75, 121.68, 83.98, 55.08, 40.37, 25.08. ESI-MS(+): m/z 438.96 [M+H]+, 460.97 [M+Na]+.

Workup

  1. customaffording B15 in 63% yield (0.09 g, 0.21 mmol)

Sources & evidence

ORD record
ord-146ae0ca431e4df1bef13b0ea7a54b97
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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