Diisopropylamine → Methyl 3-bromo-5-(5-chloropyridin-2-yl)benzoate

HRID 888406Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](B2OC(C)(C)C(C)(C)O2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.10 g, 0.29 mmol) in DMF (1.5 mL) and water (0.49 mL) were added 2-bromo-5-chloropyridine (0.17 g, 0.88 mmol), palladium(II) aceate (3.3 mg, 0.015 mmol), 3,3′3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (25.0 mg, 0.044 mmol) and diisopropylamine (0.10 mL, 0.73 mmol). The mixture was heated to 80° C. After 1 h, the mixture was filtered and the filtrate was purified by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (78 mg). MS 326.0 (M).

Workup

filtrationthe mixture was filtered
customthe filtrate was purified by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-87cd173fdbd94afd9aff1f93b1854bce
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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