Potassium Acetate → 3-(Acetoxymethyl)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)pyridin-4-ylboronic Acid
Reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([N:13]2[N:22]=[CH:21][C:20]3[C:15](=[C:16]([F:27])[CH:17]=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=3)[C:14]2=[O:28])=[N:8][CH:9]=[CH:10][C:11]=1Cl)(=[O:3])[CH3:2].CC1(C)C(C)(C)[O:33][B:32](B2OC(C)(C)C(C)(C)O2)[O:31]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])=O.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:13]2[N:22]=[CH:21][C:20]3[C:15](=[C:16]([F:27])[CH:17]=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=3)[C:14]2=[O:28])=[N:8][CH:9]=[CH:10][C:11]=1[B:32]([OH:33])[OH:31])(=[O:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 104b (150 mg, 0.37 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane), Pin2B2 (379 mg, 1.48 mmol), Pd(dppf)Cl2 (28 mg, 0.037 mmol), Xphos (35 mg, 0.074 mmol) and KOAc (108 mg, 1.11 mmol) in dioxane (5 mL) was stirred at 65° C. for 15 h under N2. The reaction mixture was concentrated. The residue was washed with DCM/PE (1 mL/20 mL) and filtered. The filtrate was concentrated to give 104c (100 mg, 66%) as yellow solid. MS-ESI: [M+H]+ 414.2
Workup
- concentrationThe reaction mixture was concentrated
- washThe residue was washed with DCM/PE (1 mL/20 mL)
- filtrationfiltered
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-dee7f1f91d9948b3b6031d38e9123649
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260415B2
Reaction notes
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