3-Aminophenylboronic acid → 3-(1-trityl-1H-imidazol-4-yl)aniline
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[N:13]=[CH:14][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[K+]>C1COCC1>[C:17]([N:15]1[CH:16]=[C:12]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH2:1])[N:13]=[CH:14]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
(3-Aminophenyl)boronic acid (1.0 g, 7.3 mmol), 4-bromo-1-trityl-1H-imidazole (2.8 g, 7.3 mmol), tri-t-butylphosphonium tetrafluoroborate (424 mg, 1.5 mmol) and KF (1.4 g, 24.1 mmol) are added into dry THF (20 mL) and argon is bubbled through the mixture for 10 min. Tris-(dibenzylideneacetone)dipalladium(0) (669 mg, 0.7 mmol) is added and the reaction mixture is sealed and heated at 60° C. for 16 hrs. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with H2O (3×100 mL), brine (100 mL), dried (Na2SO4) and concentrated. The crude product is purified by flash column chromatography using methanol/CH2Cl2 to afford the title compound (1.1 g, 36%).
Workup
- customis bubbled through the mixture for 10 min
- customthe reaction mixture is sealed
- filtrationThe solid is filtered
- additionthe filtrate is diluted with EtOAc (250 mL)
- washThe solution is washed with H2O (3×100 mL), brine (100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude product is purified by flash column chromatography
Sources & evidence
- ORD record
- ord-f2a96b2760834db0aae5f71672fee9cb
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073926B2
Reaction notes
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