Reaction #70337

ord-51e0fb53203e4f64a685adf403811cac

Reaction equation

Cc1ccc(Nc2cc(Cl)cnc2Br)c(C(=O)OC(C)(C)C)c1
Intermediate 20A
Cc1ccc(Nc2cc(Cl)cnc2Br)c(C(=O)OC(C)(C)C)c1
tert-butyl 2-(2-bromo-5-chloropyridin-3-ylamino)-5-methylbenzoate
OB(O)c1ccccc1
phenylboronic acid
→
Cc1ccc(Nc2cnc(-c3ccccc3)c(Cl)c2)c(C(=O)OC(C)(C)C)c1
tert-Butyl 2-(5-chloro-6-phenylpyridin-3-ylamino)-5-methylbenzoate

Reactants

Cc1ccc(Nc2cc(Cl)cnc2Br)c(C(=O)OC(C)(C)C)c1
Intermediate 20A
Cc1ccc(Nc2cc(Cl)cnc2Br)c(C(=O)OC(C)(C)C)c1
tert-butyl 2-(2-bromo-5-chloropyridin-3-ylamino)-5-methylbenzoate
OB(O)c1ccccc1
phenylboronic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherObtained
  2. 2
    Other(0.005 g, 3% of yield)

Procedure

Obtained (0.005 g, 3% of yield) following the procedure described in Example 8 (step A) starting with 0.230 g (0.58 mmol) of Intermediate 20A and 0.106 g (0.87 mmol) of phenylboronic acid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536165B2uspto-grants-2013_09