Potassium Acetate → (S)-1-Methyl-5-(5-(3-methylmorpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-ylboronic Acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])=[O:18])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[B:26]1(B2OC(C)(C)C(C)(C)O2)[O:30]C(C)(C)C(C)(C)[O:27]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(=O)C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:8][N:6]1[C:5](=[O:9])[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])=[O:18])=[CH:13][N:12]=2)=[CH:3][C:2]([B:26]([OH:30])[OH:27])=[CH:7]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A 100-mL round-bottomed flask equipped with a reflux condenser was charged with 136b (600 mg, 1.5 mmol), bis(pinacolato)diboron (1.2 g, 4.5 mmol), Pd2(dba)3 (137 mg, 0.15 mmol), X-phos (71 mg, 0.15 mmol), potassium acetate (294 mg, 3.0 mmol), and 1,4-dioxane (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 70° C. for 2 h. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was washed with petroleum ether to afford 136c (520 mg, 93%) as a white solid, which was used directed without further purification. MS-ESI: [M+H]+ 373.1
Workup
- customA 100-mL round-bottomed flask equipped with a reflux condenser
- customAfter three cycles of vacuum/argon flush
- filtrationIt was then filtered
- customthe filtrate was evaporated under reduced pressure
- washThe residue was washed with petroleum ether
Sources & evidence
- ORD record
- ord-09f7b2d2cfaf4ddc99f4e356156bdc2c
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669251B2
Reaction notes
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