Dichloromethane → Imidazo(1,2-a)pyridine

HRID 1971243Notes

Reaction equation

HRID 1971243 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](C(O)=O)[N:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:22]2C=CC=C[C:21]=2N=N1.C(Cl)Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[N:1]1[CH:21]=[CH:22][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=12

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3516526-Aminopyridine-2-carboxylic acid

Product 1

HCID 78960Imidazo(1,2-a)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In Scheme 2, 2-amino-6-pyridine carboxylic acid 8 is reacted with an amine 9 using a coupling agent such as, but not limited to, BOP or DMC in an organic solvent such as DCM or DMF in the presence of an organic base such as Hunig's base. The resulting amide 10 is reacted with alpha halocarbonyl 11 to give the imidazo[1,2-a]pyridine 12. Alternatively 10 can be reacted with the alpha haloaldehyde 13 to give the imidazo[1,2-a]pyridine 14.

Sources & evidence

ORD record
ord-96b0d1e03ad64ed2a4f955b004a2a723
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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