3-Aminophenylboronic acid → 3-(1-trityl-1H-imidazol-4-yl)aniline

HRID 1748351Notes

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]=1

Participants

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 h. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with water (3×100 mL), brine (100 mL), dried (Na2SO4) and concentrated. The crude material is purified by flash column chromatography using methanol in 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 water (3×100 mL), brine (100 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude material is purified by flash column chromatography

Sources & evidence

ORD record: ord-5b2fd438d4c34952a78e7f59bd411e6e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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