Triethylamine → HCID 46205449, compound

HRID 2366472Notes

Reaction equation

HRID 2366472 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C[Sn](C)(C)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C(N(CC)CC)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:12][C:4]1[CH:3]=[C:2]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 521585Tris(furan-2-yl)phosphaneHCID 11021057Pyridine, 2-(trimethylstannyl)-HCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 46205449HCID 46205449, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of EXAMPLE 50A (5 g), Pd2(dba)3 (1.5 g) and tri-2-furylphosphine (1.5 g) in DMF (100 mL) was added 2-trimethylstannyl pyridine (9.5 g) and triethylamine (2 mL). The reaction mixture was stirred at 80° C. for 18 hours, cooled and partitioned between ethyl acetate and brine. The ethyl acetate layer was separated and concentrated, and the concentrate flash chromatographed on silica gel with 1:2 ethyl acetate/hexanes.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and brine
  3. customThe ethyl acetate layer was separated
  4. concentrationconcentrated
  5. customthe concentrate flash chromatographed on silica gel with 1:2 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d9c00a420c644875bc1f14c5ddf81897
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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