Dimethylformamide → HCID 15512895, compound

HRID 1265327Notes

Reaction equation

HRID 1265327 reaction equation
CN(C)[CH:3]=[O:4].[CH3:6][O:7][C:8]([C:10]1[N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:39])([F:38])[F:37])[S:12](=[O:29])(=[O:28])[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1OS(C(F)(F)F)(=O)=O)=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH3:46][O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1B(O)O>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.[Pd].C(OCC)C.C1(C)C=CC=CC=1>[CH3:6][O:7][C:8]([C:10]1[N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:38])([F:39])[F:37])[S:12](=[O:28])(=[O:29])[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1[C:52]1[CH:53]=[C:48]([O:47][CH3:46])[CH:49]=[C:50]([O:4][CH3:3])[CH:51]=1)=[O:9]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 11124297HCID 11124297, compound

Product 1

HCID 15512895HCID 15512895, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To dimethylformamide (18 mL) was added 1,1-dioxo-4-(trifluoro-methanesulfonyloxy)-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester, (1.60 g, 3.0 mmol), palladium tetrakis(triphenyl phosphine) (0.2 g, 0.17 mmol), potassium carbonate (0.7 g, 6.0 mmol), 2-methoxy-phenyl-boronic acid (0.88 g, 6.0 mmol), and toluene (50 mL). The mixture was heated to 100° C. for 30 minutes and was filtered through a pad of Celite. The filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine, and dried over charcoal and anhydrous magnesium sulfate. The suspension was filtered and stripped to an oil which was resuspended in ethyl acetate and ethyl ether. Insoluble material from this mixture was filtered off, and the filtrate was concentrated in vacuo to an oil. The residue was chromatographed on silica gel eluted with a mixture of ethyl acetate and hexane (25:75). The appropriate fractions were concentrated in vacuo and crystallized from ethyl ether giving a solid 1.29 g, 83% yield.

Workup

  1. filtrationwas filtered through a pad of Celite
  2. washThe filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine
  3. dry with materialdried over charcoal and anhydrous magnesium sulfate
  4. filtrationThe suspension was filtered
  5. filtrationInsoluble material from this mixture was filtered off
  6. concentrationthe filtrate was concentrated in vacuo to an oil
  7. customThe residue was chromatographed on silica gel
  8. washeluted with a mixture of ethyl acetate and hexane (25:75)
  9. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-2229969d210b466f80ae3ee1971d3f5a
Source dataset
uspto-grants-2003_04
Patent number
US06545150B2

Reaction notes

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