Pyridine → HCID 51064008, compound

HRID 1048843Notes

Reaction equation

HRID 1048843 reaction equation
N1C=CC=CC=1.[C:7]([C:10]1[CH:11]=[CH:12][C:13](Br)=[N:14][CH:15]=1)(=[O:9])[CH3:8].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>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.O.C(#N)C>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:13]2[N:14]=[CH:15][C:10]([C:7](=[O:9])[CH3:8])=[CH:11][CH:12]=2)=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 156681955-Acetyl-2-bromopyridine

Product 1

HCID 51064008HCID 51064008, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

According to the general Suzuki coupling of pyridine compounds, 5-acetyl-2-bromopyridine 38 (0.394 g, 1.97 mmol), 4-tolylboronic acid (0.535 g, 3.94 mmol), Na2CO3 (0.146 g, 1.38 mmol), Pd(PPh3)2Cl2 (0.042 g, 0.06 mmol, 3% Pd), acetonitrile (7.8 mL), water (7.8 mL) were heated at 80° C. for 14 h (overnight). Following the general workup and flash chromatography (SiO2, 20 g, 5% EtOAc/hexanes) coupled ketone was obtained as a white solid 41 (0.381 g, 92%); TLC Rf=0.4 (25% EtOAc/hexanes); mp 106-107.5° C.; 1H NMR (500 MHz, CDCl3) δ 9.19 (d, J=2.2 Hz, 1H), 8.24 (dd, J=8.3, 2.3 Hz, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.79 (d, J=8.4 Hz, 1H), 7.29 (d, J=8.4 Hz, 2H), 2.63 (s, 3H), 2.40 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 196.6, 161.0, 150.2, 140.5, 136.4, 135.5, 130.5, 129.8, 127.4, 26.8, 21.5; IR (neat cm−1) 3024, 2911, 2853, 2042, 1671, 1589, 1555, 1371, 1279, 1141, 819, 762; HRMS (DART, M++H) m/z 212.1093 (calculated for C14H14NO, 212.1075).

Sources & evidence

ORD record
ord-213d3b3d4b194008b9cab465033a84ef
Source dataset
uspto-grants-2016_07
Patent number
US09382213B2

Reaction notes

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