Reaction #84091

ord-142f8f3882e1471e8bb723a571b8afe9

Reaction equation

COc1ccc2nc(Cl)ccc2c1
2-chloro-6-methoxyquinoline
N#Cc1ccc(B(O)O)s1
5-cyanothiophen-2-ylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
N#Cc1ccc(-c2ccc3cc(O)ccc3n2)s1
5-(6-hydroxyquinolin-2-yl)thiophene-2-carbonitrile

Reactants

COc1ccc2nc(Cl)ccc2c1
2-chloro-6-methoxyquinoline
N#Cc1ccc(B(O)O)s1
5-cyanothiophen-2-ylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reagents

None

Solvents

COCCOC
DME

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe two step synthesis
  2. 2
    OtherIn step 2, after quenching w/ice water
  3. 3
    Extractiona standard ethyl acetate extraction
  4. 4
    Otherwas preformed followed by purification by prep-TLC (PE: EA=1:1)

Procedure

Followed the two step synthesis shown in Scheme 1 starting with 2-chloro-6-methoxyquinoline and 5-cyanothiophen-2-ylboronic acid, with minor variations: the base used in step 1 was sodium carbonate and the solvent was DME (dimethoxyethane)/water. In step 2, after quenching w/ice water, a standard ethyl acetate extraction was preformed followed by purification by prep-TLC (PE: EA=1:1).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09433618B2uspto-grants-2016_09