2-Cyanopyridine-5-boronic acid pinacol ester → HCID 87114447, compound

HRID 1095918Notes

Reaction equation

HRID 1095918 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][N:4]=1)#[N:2].[Cl:18][C:19]1[CH:20]=[C:21]([OH:40])[CH:22]=[CH:23][C:24]=1[CH:25]([CH3:39])[C:26]([C:32]1[CH:37]=[CH:36][N:35]=[C:34]([Cl:38])[CH:33]=1)([OH:31])[C:27]([F:30])([F:29])[F:28]>CN(C1C=CN=CC=1)C.C(#N)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:24]=1[CH:25]([CH3:39])[C:26]([C:32]1[CH:37]=[CH:36][N:35]=[C:34]([Cl:38])[CH:33]=1)([OH:31])[C:27]([F:30])([F:29])[F:28])[O:40][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

6

Reactant 2

HCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 574212643-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol

Product 1

HCID 87114447HCID 87114447, compound

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Copper(II)acetate (55 mg), 2-cyanopyridine-5-boronic acid pinacol ester (CAS Reg. No. 741709-63-7, 69 mg), and DMAP (61 mg) were added to a solution of 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol (Example 19 step 5, 37 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)=468.1 [M+H+].

Workup

  1. filtrationfiltered over Celite
  2. concentrationconcentrated to an oil
  3. customThe residue was purified by prep

Sources & evidence

ORD record
ord-6d96af8449b740e4aaf6641fcb1c1b5a
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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