Diisopropylamine → HCID 68498810, compound

HRID 888393Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.Br[C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=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)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:34][C:33]1[C:28]([C:16]2[CH:15]=[C:10]([CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.80 g, 2.27 mmol) in N,N-dimethylformamide (6.8 mL) and water (2.3 mL) were added 2-bromo-3-fluoropyridine (0.44 g, 2.49 mmol), palladium acetate (25.4 mg, 0.11 mmol), 3,3′,3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (0.19 g, 0.34 mmol) and diisopropylamine (0.81 mL, 5.66 mmol). The reaction mixture was heated to 80° C. After 18 h, the mixture was cooled to ambient temperature and the solid was filtered off. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound. MS 323.0 (M+1).

Workup

temperaturethe mixture was cooled to ambient temperature
filtrationthe solid was filtered off
customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-87d8f7e81cfd4ce189b42ae1e29e7b1f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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