Potassium Acetate → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole

HRID 1618828Notes

Reaction equation

C1(N2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19]([B:22]3[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]3)=[CH:18][CH:17]=2)C=CC=CC=1.C([O-])(=[O:33])C.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:28][C:25]1([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23][B:22]([C:19]2[CH:20]=[CH:21][C:16]([C:8]3[O:33][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)=[CH:17][CH:18]=2)[O:26]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 10 (4.45 g, 16 mmol), bis(pinacolate)diborane (4.09 g, 16.1 mmol), anhydrous potassium acetate (3.14 g, 32 mmol) and Pd(dppf)Cl2 (0.48 g, 0.66 mmol) in anhydrous 1,4-dioxane (80 mL) was degassed and the resulting mixture was heated at about 85° C. for about 48 hours under argon. After cooling to room temperature, the mixture was poured into ethyl acetate (˜200 mL) and filtered. The filtrate was absorbed on silica gel and purified by column chromatography (hexanes/ethyl acetate, 4:1) to give a white solid (Compound 28) (4.15 g, in 81% yield).

Workup

customwas degassed
temperatureAfter cooling to room temperature
additionthe mixture was poured into ethyl acetate (˜200 mL)
filtrationfiltered
customThe filtrate was absorbed on silica gel
custompurified by column chromatography (hexanes/ethyl acetate, 4:1)

Sources & evidence

ORD record: ord-60c53b9e1b2248999df15cc3801a0148
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08771845B2

Reaction notes

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