Potassium Acetate → HCID 86700866, compound

HRID 881759Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[BH:17]([O-:19])[O-:18].C([O-])(=O)C.[K+].[CH3:25][CH:26]([C:28]1[CH:33]=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)[CH:29]=1)[CH3:27]>O1CCOCC1>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:17]3[O:19][C:28]([CH3:33])([CH3:29])[C:26]([CH3:27])([CH3:25])[O:18]3)=[CH:3][CH:4]=2)=[N:9][CH:10]=1)([O-:16])=[O:15]

Participants

Conditions

Temperature: 115 °C

Procedure

A flask was charged with 2-(4-chlorophenyl)-5-nitropyridine (4.48 g, 14.26 mmol), pinoco boronate (14.48 g, 57.0 mmol), potassium acetate (5.59 g, 57.0 mmol), Pd-(Xphos) (1.404 g, 1.900 mmol), X-phos (1.359 g, 2.85 mmol) and dioxane (50 ml) at room temperature. The flask was sealed, flushed with nitrogen for three times and heated at 115° C. for 72 hours. The mixture was cooled down to room temperature and diluted with dioxane (50 ml) and EtOAc (100 ml), filtered and the filtrate was concentrated. The residue was added dioxane (30 ml) and filtered, the filtrate was purified by flash chromatography (heptanes/acetone 1/2) to afford 5-nitro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (3.9 g, 84%) as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.37 (s, 9H) 7.43-8.15 (m, 7H).

Workup

customThe flask was sealed
customflushed with nitrogen for three times
temperatureThe mixture was cooled down to room temperature
additiondiluted with dioxane (50 ml) and EtOAc (100 ml)
filtrationfiltered
concentrationthe filtrate was concentrated
additionThe residue was added dioxane (30 ml)
filtrationfiltered
customthe filtrate was purified by flash chromatography (heptanes/acetone 1/2)

Sources & evidence

ORD record: ord-a6617b4382e14a40885a603ee0e7e84d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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