Diisopropylamine → Methyl 3-(5-chloropyridin-2-yl)-5-isopropenylbenzoate

HRID 888407Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-bromo-5-(5-chloropyridin-2-yl)benzoate (78.0 mg, 0.24 mmol)) in DMF (1.2 mL) and water (0.4 mL) was 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (53.9 μL, 0.29 mmol), palladium(II) acetate (2.68 mg, 0.012 mmol), 3,3′3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (20.4 mg, 0.036 mmol) and diisopropylamine (85.0 μL, 0.60 mmol) and the mixture was heated to 80° C. After 1 h, the reaction 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 (59 mg). MS 388.0 (M+1).

Workup

filtrationthe reaction 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-a0959920107b4954bb3fd74816a7ed95
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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