Water → tert-Butyl 5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate

HRID 239123Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 140 °C

Procedure

52 mg tetrakis(triphenylphosphine) palladium was added to 100 mg 2-chloropyridine, 327 mg 4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester and 0.88 mL 2 mol/L sodiumcarbonate in 2 mL dioxane. The reaction was stirred for 15 min. at 140° C. in a microwave. Water was added and the reaction was extracted with DCM. The organic layer was dried and evaporated. The residue was purified by HPLC to yield 116 mg of the desired product. Rt: 1.03 min (method L), (M+H)+: 261

Workup

extractionthe reaction was extracted with DCM
customThe organic layer was dried
customevaporated
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-b4b5d983dc1b404bbcccef81bda1a6ff
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642774B2

Reaction notes

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