Cesium carbonate → HCID 66673662, compound

HRID 423417Notes

Reaction equation

HRID 423417 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[NH:13][CH2:14][CH2:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][N:23]=1)=[O:21].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.O.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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:18][O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([N:13]2[CH2:14][CH2:15][C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[S:17][C:11]=3[C:12]2=[O:16])=[CH:24][N:23]=1)=[O:21]

Participants

9

Reactant 3

HCID 10796Cesium carbonateHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 66673217HCID 66673217, compound

Product 1

HCID 66673662HCID 66673662, compoundYield 76.5%

Reagents, catalysts & solvents 5

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Combine 2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.351 g, 1.32 mmol) and 5-bromo-pyridine-2-carboxylic acid methyl ester (Song, J.; Yee, N. K. J. Org. Chem. 2001, 66, 605) (0.345 g, 1.59 mmol) in dioxane (20 mL). Treat the solution with Xantphos (38 mg, 0.066 mmol) and Cs2CO3 (0.647 g, 1.97 mmol). Degas the reaction by purging with nitrogen for 5 min. Add Pd2(dba)3 (12 mg, 0.0132 mmol) and reflux the reaction mixture overnight. Dilute with EtOAc (100 mL) and water (100 mL). Collect the insoluble material by filtration. Wash with water (2×20 mL) and EtOAc (2×20 mL) and dry in a vacuum oven to give 0.403 g (76%) of the title compound. LC-MS/ES (35Cl) 399.0 [M+H]+.

Workup

  1. customDegas
  2. customthe reaction
  3. customby purging with nitrogen for 5 min
  4. customCollect the insoluble material
  5. filtrationby filtration
  6. washWash with water (2×20 mL) and EtOAc (2×20 mL)
  7. customdry in a vacuum oven

Sources & evidence

ORD record
ord-e6a44b1d9b2c4818b76b6482fe9e1cb8
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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