Sodium Carbonate → 5-(6-Hydroxyquinolin-2-yl)thiophene-2-carbonitrile

HRID 55813

Reaction equation

HRID 55813 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[N:3]=1.[C:14]([C:16]1[S:20][C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:19]1[S:20][C:16]([C:14]#[N:15])=[CH:17][CH:18]=1)[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 836472-Chloro-6-methoxyquinolineHCID 41987435-Cyanothiophene-2-boronic acid

Product 1

HCID 669800425-(6-Hydroxyquinolin-2-yl)thiophene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-142f8f3882e1471e8bb723a571b8afe9
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Linked notes

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