Potassium Acetate → (6-Fluoro-1,3-benzothiazol-7-yl)boronic acid

HRID 389584Notes

Reaction equation

HRID 389584 reaction equation
Br[C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:11].[B:12]1(B2OC(C)(C)C(C)(C)O2)[O:16]C(C)(C)C(C)(C)[O:13]1.C([O-])(=O)C.[K+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:11][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[CH:8][S:9][C:10]=2[C:2]=1[B:12]([OH:16])[OH:13]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 667604487-Bromo-6-fluorobenzothiazole

Product 1

HCID 66760403(6-Fluoro-1,3-benzothiazol-7-yl)boronic acidYield 71.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 7-bromo-6-fluorobenzothiazole (90.7 mg, 0.391 mmol), bis(pinacolato)diboron (149 mg, 0.587 mmol), (1,1′bis-(diphenylphosphino)-ferrocene) palladium dichloride (15.9 mg, 0.0217 mmol), and potassium acetate (76.7 mg, 0.782 mmol) in 1,4-dioxane (1.9 mL) was heated to 85° C. for 24 h. The reaction mixture was concentrated and was then purified by ISCO chromatography (0 to 50% EtOAc:hexane) to give afford 55.3 mg of the title compound as an off-white solid. MS (ESI): 198.02 [M+H]+; HPLC tR=1.18 min (TOF: polar—3 min).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas then purified by ISCO chromatography (0 to 50% EtOAc:hexane)
  3. customto give

Sources & evidence

ORD record
ord-a168ca70a4ae4b12a35c5af2ee5fceea
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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