Tetrahydrofuran → HCID 69046893, compound

HRID 69979Notes

Reaction equation

HRID 69979 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-].[CH:14]1([Zn+])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1COCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 45480453Methyl 3-amino-6-bromopyridine-2-carboxylateHCID 178418970HCID 178418970, compound

Product 1

HCID 69046893HCID 69046893, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

A solution of methyl 3-amino-6-bromopicolinate (1.0 equiv.), cyclohexyl zincbromide 0.5 M solution in THF (1.5 equiv.), and tetrakis(triphenylphosphine)-palladium(0) (0.05 equiv.) was stirred at 50° C. for 15 minutes. The reaction was filtered and washed with EtOAc. The organic was washed with H2O (100 mL), NaCl(sat.) (50 mL), dried over MgSO4, and the volatiles were removed in vacuo. The product was purified on silica utilizing the Isco 0-65% gradient of hexane/EtOAc to yield methyl 3-amino-6-cyclohexylpicolinate (98%). LCMS (m/z): 235.2 (MH+); LC Rt=1.89 min.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with EtOAc
  3. washThe organic was washed with H2O (100 mL), NaCl(sat.) (50 mL)
  4. dry with materialdried over MgSO4
  5. customthe volatiles were removed in vacuo
  6. customThe product was purified on silica utilizing the Isco 0-65% gradient of hexane/EtOAc

Sources & evidence

ORD record
ord-0d1a1e8bad484d80a07f606ff2bbf352
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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