Benzo(B)Thiophene-2-Boronic Acid → HCID 178432461, compound

HRID 2233315Notes

Reaction equation

HRID 2233315 reaction equation
Br[C:2]1[S:3][C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[NH:17][O:18][C:19](=[O:21])[N:20]=3)=[C:12]([Cl:22])[CH:11]=2)=[C:5]([CH3:7])[N:6]=1.[S:23]1[C:27](B(O)O)=[CH:26][C:25]2[CH:31]=[CH:32][CH:33]=[CH:34][C:24]1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[S:23]1[C:27]([C:2]2[S:3][C:4]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[NH:17][O:18][C:19](=[O:21])[N:20]=4)=[C:12]([Cl:22])[CH:11]=3)=[C:5]([CH3:7])[N:6]=2)=[CH:26][C:25]2[CH:31]=[CH:32][CH:33]=[CH:34][C:24]1=2

Participants

6

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10796Cesium carbonateHCID 178432454HCID 178432454, compound

Product 1

HCID 178432461HCID 178432461, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-[4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-phenyl]-2H-[1,2,4]oxadiazol-5-one (300 mg, 0.7 mmol), Benzo[b]thiophene-2-boronic acid (142 mg, 0.8 mmol) and cesium carbonate (730 mg, 2.2 mol) in dimethylformamide (5 mL) and water (1 mL) is degassed using a stream of argon for 15 min. Tetrakis-triphenylphosphine-palladium (0) (34 mg, 0.03 mmol) is added and the mixture is warmed to 40° C. for 4 hours. The solvent is removed under reduced pressure and the residue is taken up in water (10 mL) and ethylacetate (30 mL). The phases are separated and the water phase is additionally extracted two-times with ethylacetate. The combined organic phases are dried over MgSO4 and the solvent is removed under reduced pressure. The crude product is purified using reverse phase HPLC to obtain 147 mg 3-[4-(2-Benzo[b]thiophen-2-yl-4-methyl-thiazol-5-ylmethoxy)-2-chloro-phenyl]-2H-[1,2,4]oxadiazol-5-one as an amorphous lyophilisate.

Workup

  1. customis degassed
  2. customfor 15 min
  3. customThe solvent is removed under reduced pressure
  4. customThe phases are separated
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. customthe solvent is removed under reduced pressure
  7. customThe crude product is purified

Sources & evidence

ORD record
ord-b59bfa7080d54983bcec51a027268d52
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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