Tetramethyltin → HCID 90412282, compound

HRID 2175966Notes

Reaction equation

HRID 2175966 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[C:5](Br)=[CH:4][CH:3]=1.[CH3:13][Sn](C)(C)C.[Li+].[Cl-]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11661Tetramethyltin2×HCID 433294Lithium Chloride2×HCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylate

Product 1

HCID 90412282HCID 90412282, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To methyl 6-amino-3-bromopicolinate (500 mg, 2.2 mmol), tetramethylstannane (900 μL, 6.5 mmol) and LiCl (354 mg, 8.7 mmol) in DMF (6 mL) was added Pd(PPh3)4 (76 mg, 10 mol %). The reaction mixture was heated at 110° C. for 3 h. Additional tetramethylstannane, LiCl and Pd(PPh3)4 were added and heating continued for 6 h. Purification via silica gel chromatography (0-20% MeOH in DCM) gave the title compound.

Workup

  1. temperatureheating
  2. customPurification via silica gel chromatography (0-20% MeOH in DCM)

Sources & evidence

ORD record
ord-44ad62657bea4b8fbcbf90330fb0d38d
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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