Dichloromethane → (6-ethyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)boronic acid

HRID 1778740Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH2:10][N:9]([CH2:11][CH3:12])[C:8](=[O:13])[C:5]2=[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+].ClCCl>O1CCOCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:11]([N:9]1[CH2:10][C:4]2[C:5](=[N:6][CH:7]=[C:2]([B:17]([OH:18])[OH:16])[CH:3]=2)[C:8]1=[O:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-bromo-6-ethyl-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one (240 mg, 1.0 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (250 mg, 1.0 mmol), potassium acetate (290 mg, 3.0 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complexed with dichloromethane (1:1) (30 mg, 0.04 mmol) in 1,4-dioxane (10 mL) was degassed and stirred at 100° C. for 6 h. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.11 g). LCMS (M+H)+=207.1.

Workup

customwas degassed
temperatureAfter cooling it
concentrationwas concentrated under reduced pressure
customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record: ord-bf5f12b79fa34619b3b0fc51bd4d8aac
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266892B2

Reaction notes

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