4-Bromopyridinium chloride → HCID 17963851, compound

HRID 1375028Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:8]=[C:9](OB(O)O)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=2)=[N:3]1.Cl.Br[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>C(=O)([O-])[O-].[Na+].[Na+].COCCOC.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>[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:8]=[C:9]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=2)=[N:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-5-(trifluoromethyl)phenylboroic acid (0.58 g) and 4-bromopyridine hydrochloride (0.39 g) in a mixture of sodium carbonate aqueous solution (2M, 6 ml) and 1,2-dimethoxyethane (4 ml) was added tetrakis(triphenylphosphine)palladium (0.116 g) under nitrogen atmosphere. After stirring at 80° C. for 12 hours, the mixture was quenched with water and extracted with ethyl acetate twice. The combined extracts were dried over magnesium sulfate, evaporated, and purified with column chromatography (silica gel, ethyl acetate:hexane=1:3–2:1–1:2) to give 4-[3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-5-(trifluoromethyl)phenyl]pyridine (0.61 g) as a syrup.

Workup

customthe mixture was quenched with water
extractionextracted with ethyl acetate twice
dry with materialThe combined extracts were dried over magnesium sulfate
customevaporated
custompurified with column chromatography (silica gel, ethyl acetate:hexane=1:3–2:1–1:2)

Sources & evidence

ORD record: ord-87461a9bc9cf4be4a4f599c9f650e99f
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166598B2

Reaction notes

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