Reaction equation
BrC1C(=O)[O:4][C:5]2[C:10]([C:11]=1C)=[CH:9][CH:8]=[C:7](O)[CH:6]=2.B(O)(O)O.[C:19]([O-:22])([O-])=O.[Na+].[Na+].[CH3:25][N:26]([CH:28]=[O:29])C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:10]=[CH:11][C:25]2[NH:26][C:28](=[O:29])[CH:9]=[CH:8][C:7]=2[C:6]=1[CH:19]=[O:22]Participants
6
Conditions
- Temperature
- 90 °C
Procedure
Compound 1 (15 g, 46 mmol), the boric acid (8.7 g, 50.6 mmol), Pd(PPh3)4 (1.88 g, 2.3 mmol), Na2CO3 (12.1 g, 115 mmol) were added to DMF (250 mL). The reaction mixture was degassed with N2 for three times, and then heated to 90° C. for 16 h. After cooled to RT, the solvent was concentrated, the residue was dissolved in sat Na2CO3 (150 mL). The aqueous was washed with DCM (100 mL×4), and then acidified by con.HCl to pH to ˜4. The result precipitate was collected by filtration, triturated with hot EA (50 mL), afforded compound 2 (6.5 g, 42%) as yellow solid. 1HNMR (DMSO-d6, 400 MHz): δ 10.55 (s, 1H), 7.71 (d, J=4.0 Hz, 1H), 7.24 (s, 1H), 7.19 (d, J=4.0 Hz, 1H), 6.86 (s, 1H), 3.88 (s, 3H), 2.45 (s, 3H).
Workup
- customThe reaction mixture was degassed with N2 for three times
- temperatureAfter cooled to RT
- concentrationthe solvent was concentrated
- dissolutionthe residue was dissolved in sat Na2CO3 (150 mL)
- washThe aqueous was washed with DCM (100 mL×4)
- filtrationThe result precipitate was collected by filtration
- customtriturated with hot EA (50 mL)
Sources & evidence
- ORD record
- ord-fd2c5cdf448a4fdaaf8662ae7684b07b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040714B2
Linked notes
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