Cesium carbonate → HCID 58408403, compound

HRID 1948560Notes

Reaction equation

HRID 1948560 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9](I)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[N:18][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.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]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:16]2[CH:17]=[N:18][CH:19]=[C:14]([CH3:13])[CH:15]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27627085-Methylpyridine-3-boronic acidHCID 50998202Methyl 2-bromo-5-iodobenzoate

Product 1

HCID 58408403HCID 58408403, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-bromo-5-iodobenzoate (2-2, 2.0 g, 5.87 mmol, 1.0 equiv), 5-methylpyridine-3-boronic acid (0.803 g, 5.87 mmol, 1.0 equiv), Cs2CO3 (6.69 g, 20.53 mmol, 3.5 equiv) and PdCl2(dppf) (0.429 g, 0.587 mmol, 0.1 equiv) was made in DMF (30 mL) and stirred at room temperature overnight. The reaction mixture was partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (25 to 75% EtOAc in hexanes) to afford the product (2-3) as a solid. ESI+ MS [M+H]+ C14H12BrNO2: 307.8 found, 307.1 required.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. washThe combined organics were washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by normal phase column chromatography (25 to 75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c3a35a20d84f44da87b9f91e9e40848e
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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