Hydrochloric Acid → 4-Amino-5-cyano-6-thien-3-ylpyridine-2-carboxylic acid

HRID 1364570Notes

Reaction equation

HRID 1364570 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([C:12]#[N:13])=[C:7](OCC)[N:6]=1)=[O:4].[S:17]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18]1.C([O-])([O-])=O.[Na+].[Na+].Cl>COC.O.C(O)C>[NH2:11][C:9]1[C:8]([C:12]#[N:13])=[C:7]([C:19]2[CH:20]=[CH:21][S:17][CH:18]=2)[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 40151899Methyl 4-amino-5-cyano-6-ethoxypicolinate

Product 1

HCID 669209934-Amino-5-cyano-6-thien-3-ylpyridine-2-carboxylic acidYield 21%

Reagents, catalysts & solvents 1

HCID 86620092Dimethyl ether water ethanolSolvent

Procedure

A suspension of Example 181D (212 mg, 1.0 mmol), 3-thiopheneboronic acid (134 mg, 1.05 mmol), dichlorobis(triphenylphosphine)-palladium(II) (Ph3P)2PdCl2 (7 mg, 0.01 mmol), and Na2CO3 (212 mg, 2.0 mmol) in dimethyl ether: water: ethanol (7:3:2, 4 mL) was heated at 150° C. for 10 minutes in a microwave reactor. The crude mixture was acidified with 2N HCl (2 mL) and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. It was triturated with acetonitrile to provide the titled compound (51 mg, 21% yield).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customIt was triturated with acetonitrile

Sources & evidence

ORD record
ord-d450fab6edce4f47b164fbe5061a9ef6
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

Loading…