Dichloromethane → 2-Amino-7-fluoro-3-morpholinoquinolin-6-ylboronic acid

HRID 1029019Notes

Reaction equation

C([O-])(=O)C.[K+].C(Cl)Cl.CC1(C)C(C)(C)[O:13][B:12](B2OC(C)(C)C(C)(C)O2)[O:11]1.Br[C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[F:38])[N:34]=[C:33]([NH2:39])[C:32]([N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[CH:31]2>CN(C=O)C>[NH2:39][C:33]1[C:32]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[CH:31][C:30]2[C:35](=[CH:36][C:37]([F:38])=[C:28]([B:12]([OH:13])[OH:11])[CH:29]=2)[N:34]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A microwave vessel was charged with potassium acetate (0.34 g, 3.46 mmol), [1,1′-bis(dppf)]dichloropalladium(II) complex with CH2Cl2 (0.038 g, 0.052 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (0.211 g, 0.831 mmol), 6-bromo-7-fluoro-3-morpholinoquinolin-2-amine (0.226 g, 0.693 mmol), and DMF (2.2 mL). The vessel was purged with argon, sealed, and heated by microwave radiation for 30 min at 125° C. The reaction was diluted with EtOAc (10 mL), and the suspension was filtered through celite rinsing with EtOAc. The filtrate was concentrated. The residue was purified by column chromatography on silica gel (25 mL) which had been deactivated with Et3N (2.5 mL) using 3% MeOH/DCM to afford 2-amino-7-fluoro-3-morpholinoquinolin-6-ylboronic acid.

Workup

customThe vessel was purged with argon
customsealed
additionThe reaction was diluted with EtOAc (10 mL)
filtrationthe suspension was filtered
washthrough celite rinsing with EtOAc
concentrationThe filtrate was concentrated
customThe residue was purified by column chromatography on silica gel (25 mL) which

Sources & evidence

ORD record: ord-4868332f76a845a280925b63c4d63bbf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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