Potassium Carbonate → HCID 71138807, compound

HRID 539520Notes

Reaction equation

HRID 539520 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]2=[O:15])=[CH:4][CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:17]=[CH:16][C:5]([CH2:6][N:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]3=[O:15])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 71138918HCID 71138918, compound

Product 1

HCID 71138807HCID 71138807, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Reaction of 145 (0.25 g, 0.85 mmol), pyrdin-4-ylboronic acid (0.12 g, 1.02 mmol), 2M aq. K2CO3 (0.23 g, 1.69 mmol), Pd(PPh3)4 (2.5 mol %) according to method described for synthesis of 146a within 18 h afforded 203 mg of 146i (82%) of white solid. 1H NMR (400 MHz, CDCl3) δ 8.54 (dd, J=4.5, 1.6 Hz, 2H), 7.48 (m, 2H), 7.36 (m, 4H), 6.87 (dd, J=6.9, 1.7 Hz, 1H), 6.53 (dd, J=7.4, 1.6 Hz, 1H), 6.03 (t, J=7.2 Hz, 1H), 5.13 (s, 2H), 3.72 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 157.82, 150.32, 150.01, 149.90, 147.40, 137.31, 137.28, 128.57, 127.68, 127.04, 121.22, 111.90, 104.98, 55.57, 51.42. HRMS (EI) calcd for C18H16N2O2 [M]+ 292.1212. found 292.1205.

Sources & evidence

ORD record
ord-604170ec9bc64516a866fa0933cc3636
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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