Sodium Carbonate → HCID 66864301, compound

HRID 1748594Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].O.C(=O)(O)[O-].[Na+]>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.O1CCOCC1>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH:18]=[C:19]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 90 °C

Procedure

To 2,5-dibromopyridine (5.0 g), tetrakis(triphenylphosphine)palladium(0) (1.22 g), and N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (8.16 g) were added 1,4-dioxane (42 ml) and 2M aqueous solution of sodium carbonate (26 ml), and stirred at 90° C. for 7 hours. To the reaction solution was added saturated sodium bicarbonate water, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with basic silica gel chromatography (n-hexane/ethyl acetate) to give 4-(5-bromopyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester (6.45 g) as a pale yellow oil.

Workup

extractionextracted with ethyl acetate
dry with materialthe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated in vacuo
customThe obtained residue was purified with basic silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-3142aadad7a048979bb4ba8f805ffa58
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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