Water → HCID 58545066, compound
Reaction equation
C(OC(=O)[CH:5]([N:11]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[C:12]1[CH:17]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:15]=[CH:14][N:13]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])C.[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.[C:43](=[O:46])([O-])[O-:44].[K+].[K+].O.[C:50]1(C)C=CC=C[CH:51]=1>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>[CH2:50]([O:44][C:43](=[O:46])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:11]([C:12]1[CH:17]=[C:16]([C:37]2[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=2)[CH:15]=[CH:14][N:13]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH3:51]Participants
7
Procedure
Compound II (54 mg, 0.113 mmol), Pd(PPh3)4 (13 mg, 0.011 mmol), 4-fluorophenylboronic acid (32 mg, 0.23 mmol) and potassium carbonate (63 mg, 0.45 mmol) were stirred in toluene (1.5 mL) and water (0.7 mL) at 120° C. under microwave irradiation (300 W) for 30 min. The reaction mixture was then poured onto brine (5 mL) and extracted with EtOAc (3×5 mL). The organic phases were combined then dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (90:10 then 80:20) to furnish III as a colourless oil (34 mg, 71%).
Workup
- additionThe reaction mixture was then poured onto brine (5 mL)
- extractionextracted with EtOAc (3×5 mL)
- dry with materialThe organic phases were combined then dried over MgSO4
- filtrationfiltered
- customsubsequently evaporated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
- washeluting with hexane/EtOAc (90:10
Sources & evidence
- ORD record
- ord-aadc471f59f6430a92633970dd8d34b0
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340503B2
Reaction notes
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