Potassium Acetate → {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid

HRID 1695745Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:18][B:17](B2OC(C)(C)C(C)(C)O2)[O:16]1.C([O-])(=O)C.[K+]>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].O1CCOCC1>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([B:17]([OH:18])[OH:16])=[CH:3][C:4]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide (1 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (0.98 g), potassium acetate (1.03 g) and Pd(dppf)Cl2 (0.256 g) were weighed to a 10-20 ml microwave vial and 1,4-dioxane (10 ml) was added. The reaction was heated at 80° C. for a total of 2 h in the microwave. Further 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (0.489 g), potassium acetate (0.516 g) and Pd(dppf)Cl2 (0.128 g) were added and the reaction was heated at 90° C. for a total of 1.5 h in the microwave. The reaction was filtered through a hydrophobic frit then evaporated to dryness. The residue was purified on the ISCO companion using an 80 g silica cartridge, and a gradient of 2-8% methanol in DCM (containing 1% ammonia) over 25 mins. Pure fractions were combined and evaporated to dryness, then dried on the vacuum line to give title compound (439 mg).

Workup

temperaturethe reaction was heated at 90° C. for a total of 1.5 h in the microwave
filtrationThe reaction was filtered through a hydrophobic frit
customthen evaporated to dryness
customThe residue was purified on the ISCO companion
customevaporated to dryness
customdried on the vacuum line

Sources & evidence

ORD record: ord-15f12f37333d468d8af4b3c38cd1fec9
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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