Sodium Carbonate → HCID 22662095, compound

HRID 392866Notes

Reaction equation

HRID 392866 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12](B(O)O)=[C:11]([O:20][CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]2[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]2[CH3:35])[N:24]=1.C(=O)([O-])[O-].[Na+].[Na+].CO.O>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.C(O)C.O.O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]3[CH3:35])[N:24]=2)=[C:11]([O:20][CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 155127672-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridineHCID 22242641Methanol--water (1/1)HCID 22662103HCID 22662103, compound

Product 1

HCID 22662095HCID 22662095, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 19096565Water ethanolSolvent2×

Procedure

Reacting the 4-benzyloxy-5-ethyl-2-methoxy-phenylboronic acid (5) with 2-bromo-6-(2,5-dimethylpyrrol-1-yl)pyridine, sodium carbonate and tetrakis(triphenylphosphine)palladium(0) in a polar solvent such as methanol/water, ethanol/water, or tetrahydrofuran (THF)/water, preferably ethanol/water, at a temperature from about room temperature to about the reflux temperature of the reaction mixture, preferably at about the reflux temperature, yields 2-(4-benzyloxy-5-ethyl-2-methoxy-phenyl)-6-(2,5-dimethyl-pyrrol-1-yl)-pyridine (6).

Sources & evidence

ORD record
ord-003a8f3648274d979229452ce6612ed6
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

Loading…