Diisopropylamine → Methyl 3-isopropenyl-5-(5-methylpyridin-2-yl)benzoate

HRID 888397Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:19](B1OC(C)(C)C(C)(C)O1)([CH3:21])=[CH2:20].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)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([CH3:21])=[CH2:20]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (1.00 g, 3.27 mmol) in N,N-dimethylformamide (9.80 mL) and water (3.27 mL) was 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.921 mL, 4.90 mmol), palladium(II) acetate (37.0 mg, 0.163 mmol), 3,3′3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (278 mg, 0.490 mmol) and diisopropylamine (1.16 mL, 8.17 mmol) and the mixture was heated to 80° C. After 50 min, the reaction was allowed to cool to ambient temperature and filtered. Purification by reverse phase chromatography (C-18, 90% water/acetonitrile→40% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (864 mg). MS 268.2 (M+1).

Workup

temperatureto cool to ambient temperature
filtrationfiltered
customPurification by reverse phase chromatography (C-18, 90% water/acetonitrile→40% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-195a0940c91e44b29ac8d50b1d12a004
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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