Sodium Carbonate → N-(cyclopropyl(5-(2-methoxyphenyl)pyridin-3-yl)methyl)ethanesulfonamide

HRID 391302Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[C:15]([CH:19]([CH:26]2[CH2:28][CH2:27]2)[NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])[CH:16]=[N:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:26]1([CH:19]([C:15]2[CH:16]=[N:17][CH:18]=[C:13]([C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:2][CH3:1])[CH:14]=2)[NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-methoxyphenylboronic acid (48 mg, 0.31 mmol), N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide (100 mg, 0.31 mmol), PdCl2(PPh3)2 (18 mg, 0.02 mmol) and Na2CO3 (2 M in water, 0.39 mL, 0.78 mmol) in DMF(2 mL) was heated at 100° C. for 2 h. After concentration, the resulting residue was dissolved in DCM and filtered. The filtrates were concentrated and purified by flash column (EtOAc/Heptane, v/v, 0-40%) to give the title compound (38 mg, 35%); ESI-MS m/z: 347 [M+1]+. 1H-NMR (MeOD, 400 MHz) δ 8.75 (1H, bs), 8.61 (1H, bs), 8.17 (1H, bs), 7.46 (1H, t, J=8.0 Hz), 7.27 (1H, dd, J=8.0, 2.4 Hz), 7.24 (1H, t, J=2.4 Hz), 7.05 (1H, dd, J=8.0, 2.4 Hz), 3.94 (1H, d, J=9.2 Hz), 3.91 (3H, s), 3.03-2.89 (2H, m), 1.35-1.29 (1H, m), 1.29 (3H, t, J=7.2 Hz), 0.81-0.75 (1H, m), 0.676-0.60 (2H, m), 0.53-0.48 (1H, m)

Workup

concentrationAfter concentration
dissolutionthe resulting residue was dissolved in DCM
filtrationfiltered
concentrationThe filtrates were concentrated
custompurified by flash column (EtOAc/Heptane, v/v, 0-40%)

Sources & evidence

ORD record: ord-137a49159d664d6199fbe24620d455a8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383827B2

Reaction notes

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