Dichloromethane → HCID 66616460, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[N:14]=[C:15](OS(C(F)(F)F)(=O)=O)[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>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.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([C:24]([CH3:25])([CH3:27])[CH3:26])[N:14]=[C:15]([C:34]3[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=3)[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To the product from Step B (0.17 g, 0.39 mmol) was added 4-fluorophenylboronic acid (0.082 g, 0.586 mmol), K3PO4 (0.124 g, 0.584 mmol), Pd(Cl)2dppf.CH2Cl2 (0.018 g, 0.022 mmol) and dppf (0.008 g, 0.014 mmol). The mixture was evacuated with N2, dioxane (4 mL) was added and the mixture was heated at reflux for 2 h. After cooling to room temperature (rt), the mixture was diluted with Et2O, filtered through a small SiO2 plug, and the filtrate was concentrated. The resulting residue was purified via SiO2 chromatography (5-30% EtOAc/hexanes) to give 0.134 g (89%) of the title compound. MS (ESI): exact mass calcd. for C22H28FN3O2, 385.22; m/z found, 386.4 [M+H]+. 1H NMR (CDCl3): 7.60 (dd, J=5.4, 8.8, 2H), 7.17-7.14 (m, 2H), 4.59 (s, 2H), 3.76 (t, J=6.1, 2H), 3.09 (t, J=6.1, 2H), 1.44 (s, 9H), 1.41 (s, 9H).
Workup
- customThe mixture was evacuated with N2, dioxane (4 mL)
- additionwas added
- temperaturethe mixture was heated
- temperatureat reflux for 2 h
- additionthe mixture was diluted with Et2O
- filtrationfiltered through a small SiO2 plug
- concentrationthe filtrate was concentrated
- customThe resulting residue was purified via SiO2 chromatography (5-30% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-f68b2839bb914fb399b8f1418dc08078
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618288B2
Reaction notes
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