[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetonitrile → HCID 66697376, compound

HRID 2386795Notes

Reaction equation

[C:1]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1)#[N:2].[Cl:20][C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:22]=1[CH:28]([CH3:47])[C:29]([C:35]1[CH:46]=[CH:45][C:38]2[N:39]([CH3:44])[C:40](=[O:43])[N:41]([CH3:42])[C:37]=2[CH:36]=1)([OH:34])[C:30]([F:33])([F:32])[F:31]>CN(C1C=CN=CC=1)C.C(#N)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:20][C:21]1[CH:26]=[C:25]([CH:24]=[CH:23][C:22]=1[CH:28]([CH3:47])[C:29]([C:35]1[CH:46]=[CH:45][C:38]2[N:39]([CH3:44])[C:40](=[O:43])[N:41]([CH3:42])[C:37]=2[CH:36]=1)([OH:34])[C:30]([F:33])([F:31])[F:32])[O:27][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:1]#[N:2])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Copper(II)acetate (26 mg), 4-cyanomethoxy-phenylboronic acid pinacol ester (CAS Reg. No. 475272-13-0, 38 mg), and DMAP (30 mg) were added to a solution of 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (Example 85, 20 mg) in acetonitrile (3 ml). The mixture was stirred with molecular sieves under air atmosphere for 4 h at 80° C., and then filtered over Celite concentrated to an oil. The residue was purified by prep. HPLC (C18-column, solvent gradient 20-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (24 mg) as a white solid. MS (m/e)=546.1 [M+H+].

Workup

filtrationfiltered over Celite
concentrationconcentrated to an oil
customThe residue was purified by prep

Sources & evidence

ORD record: ord-64db6f1f865f4659b9ec2446942c4776
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268820B2

Reaction notes

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