Tetrahydrofuran → Methyl 3-amino-6-(thiazol-2-yl)picolinate

HRID 69964Notes

Reaction equation

HRID 69964 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[Br-].[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[Zn+].C1COCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:15]2[S:14][CH:18]=[CH:17][N:16]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 45480453Methyl 3-amino-6-bromopyridine-2-carboxylateHCID 178419763HCID 178419763, compound

Product 1

HCID 66652946Methyl 3-amino-6-(thiazol-2-yl)picolinateYield 51%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

A solution of methyl 3-amino-6-bromopicolinate (1.0 equiv.), 2-thiazolylzinc bromide 0.5 M solution in THF (3.0 equiv.), and Pd(dppf)Cl2-DCM (0.05 equiv.) was stirred at 80° C. for 1.5 hours. The reaction was filtered and washed with EtOAc. The organic was washed with H2O (100 mL), and further washed with NaCl(sat.) (50 mL), dried over MgSO4, and the volatiles were removed in vacuo. The product was crystallized with hexane/EtOAc (1:1) to yield methyl 3-amino-6-(thiazol-2-yl)picolinate (51%). LCMS (m/z): 236.1 (MH+); LC Rt=2.3 min.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with EtOAc
  3. washThe organic was washed with H2O (100 mL)
  4. washfurther washed with NaCl(sat.) (50 mL)
  5. dry with materialdried over MgSO4
  6. customthe volatiles were removed in vacuo
  7. customThe product was crystallized with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-671fb9d3bff14676bd15278f99f7f457
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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