Ethanol → HCID 71203599, compound

HRID 1844547Notes

Reaction equation

HRID 1844547 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[C:21]1[CH:22]=[C:23]([C:29]2[S:33][C:32]([C:34]([O:36]CC)=[O:35])=[N:31][C:30]=2[CH3:39])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][O:27][C:26]1[C:21]([C:8]2[CH:9]=[CH:10][C:5]([S:2](=[O:4])(=[O:3])[NH2:1])=[CH:6][CH:7]=2)=[CH:22][C:23]([C:29]2[S:33][C:32]([C:34]([OH:36])=[O:35])=[N:31][C:30]=2[CH3:39])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 71185511HCID 71185511, compound

Product 1

HCID 71203599HCID 71203599, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
92.5 °C

Procedure

4-aminosulfonylbenzene boronic acid (1.15 g, 5.73 mmol) and potassium carbonate (1.97 g, 14.31 mmol) were added to a solution of ethyl 5-(3-bromo-4-methoxyphenyl)-4-methylthiazole-2-carboxylate (Step 1, 1.70 g, 4.77 mmol) in a mixture of toluene:ethanol (15 ml:40 ml) in a tube at 25° C. Nitrogen gas was bubbled through reaction mixture for 15 minutes and to it was added tetrakis(triphenylphosphine)palladium (0) (0.28 g, 0.24 mmol) under nitrogen and the tube was sealed. The reaction mixture was heated at 90-95° C. for 18 hr with stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite. The celite cake was then washed with 10% methanol in dichloromethane (3×30 ml). The filtrate was dried over sodium sulphate and was concentrated under reduced pressure to obtain the title compound 8b (1.70 g, 88.08%).

Workup

  1. customat 25° C
  2. customNitrogen gas was bubbled through reaction mixture for 15 minutes and to it
  3. customthe tube was sealed
  4. temperatureThe reaction mixture was then cooled to 25° C.
  5. filtrationfiltered through celite
  6. washThe celite cake was then washed with 10% methanol in dichloromethane (3×30 ml)
  7. dry with materialThe filtrate was dried over sodium sulphate
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9509eac415974d62b977296f10855713
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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