Potassium Carbonate → HCID 70058022, compound

HRID 1449542Notes

Reaction equation

HRID 1449542 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:34]=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)[S:7](=[O:24])(=[O:23])[C:8]2[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=2[C:10]=1OS(C(F)(F)F)(=O)=O)=[O:4].[CH3:35][O:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CN(C=O)C.C(OCC)(=O)C.[Pd]>[O:30]1[C:29]2[CH:33]=[CH:34][C:26]([CH2:25][N:6]3[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:10]([C:39]4[CH:40]=[C:41]([O:45][CH3:46])[C:42]([O:43][CH3:44])=[C:37]([O:36][CH3:35])[CH:38]=4)[C:9]4[CH:19]=[CH:20][CH:21]=[CH:22][C:8]=4[S:7]3(=[O:23])=[O:24])=[CH:27][C:28]=2[O:32][CH2:31]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 53908012HCID 53908012, compound

Product 1

HCID 70058022HCID 70058022, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21735183Dimethylformamide tolueneSolvent

Procedure

2-Benzo[1,3]dioxol-5-ylmethyl-1,1-dioxo-4-(trifluoromethanesulfonyloxy)-1,2-dihydro-1λ6 -benzo[e][1,2]thiazine-3-carboxylic acid methyl ester was taken up in toluene/DMF (10 mL/2 mL) and treated with (3,4,5-trimethoxy)phenylboronic acid (0.35 g, 1.65 mmol), potassium carbonate (0.23 g, 1.67 mmol), and Pd° (PPh3)4 (0.19 g, 0.16 mmol). The reaction mixture was heated to reflux for 2 hours, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3, brine, dried over magnesium sulfate, and the solvent evaporated. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate 1:1. The resulting oil was treated with diethyl ether, the precipitated solid collected, and dried to give the product as an off-white solid;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. washwashed with sat. aq. NaHCO3, brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with hexane/ethyl acetate 1:1
  8. additionThe resulting oil was treated with diethyl ether
  9. customthe precipitated solid collected
  10. customdried

Sources & evidence

ORD record
ord-f22b5c5b2292407493cf50df89965e61
Source dataset
uspto-grants-1997_02
Patent number
US05599811

Reaction notes

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