Sodium Carbonate → HCID 49820276, compound

HRID 391303Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:13]=[C:14]([CH:18]([CH:25]2[CH2:27][CH2:26]2)[NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:15]=[N:16][CH:17]=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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]([CH:18]([CH:25]2[CH2:27][CH2:26]2)[NH:19][S:20]([CH2:23][CH3:24])(=[O:21])=[O:22])[CH:15]=[N:16][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chlorophenylboronic acid (24 mg, 0.16 mmol), N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide (50 mg, 0.16 mmol), PdCl2(PPh3)2 (9 mg, 0.01 mmol) and Na2CO3 (2 M in water, 0.16 mL, 0.32 mmol) in DMF(1.5 mL) was heated at 100° C. for 2 h. After concentration, the 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 (12 mg, 23%); ESI-MS m/z: 351 [M+1]+, 1H-NMR (MeOD, 400 MHz) δ 8.65 (1H, d, J=2.0 Hz), 8.55 (1H, d, J=2.0 Hz), 8.04 (1H, t, J=2.0 Hz), 7.61-7.58 (1H, m), 7.48-7.44 (3H, m), 4.29 (1H, d, 0.1=8.8 Hz), 3.02-2.89 (2H, m), 1.34-1.28 (1H, m), 1.28 (1H, t, J=7.2 Hz), 0.80-0.75 (1H, m), 0.67-0.60 (2H, m), 0.51-0.47 (1H, m)

Workup

concentrationAfter concentration
dissolutionthe 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-74d9264cd2a0406383f0c54bb538401a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383827B2

Reaction notes

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