2-Bromothiazole → HCID 67107589, compound

HRID 2177715Notes

Reaction equation

HRID 2177715 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14](B3OC(C)(C)C(C)(C)O3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:33]1[S:34][CH:35]=[CH:36][N:37]=1.O.[F-].[K+].[Br-].[Na+]>FC(F)(F)C1C=CC=CC=1.[Pd].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>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([C:33]3[S:34][CH:35]=[CH:36][N:37]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 764302-BromothiazoleHCID 253881Sodium BromideHCID 23675105Potassium fluoride hydrateHCID 67107706HCID 67107706, compound2×

Product 1

HCID 67107589HCID 67107589, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of methyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Intermediate 59, 0.284 g), tetrakis-(triphenylphosphine) palladium (0.05 g), 2-bromothiazole (0.267 g), potassium fluoride monohydrate (0.25 g) and sodium bromide (0.117 g) in α,α,α-trifluorotoluene (5 ml) was degassed and then heated in the microwave at 175° C. for 2 hours. Ethyl acetate was added and the mixture was filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give methyl 6-benzenesulphonylmethyl-2-methoxy-3-(thiazol-2-yl)-benzoate (0.05 g) as a brown oil.

Workup

  1. customwas degassed
  2. additionEthyl acetate was added
  3. filtrationthe mixture was filtered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Sources & evidence

ORD record
ord-552dfca6b174425491c83cc1d9603258
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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