Potassium Carbonate → 7-Bromo-5-(3-fluorophenyl)-1,2,3-benzothiadiazole

HRID 389596Notes

Reaction equation

HRID 389596 reaction equation
[Br:1][C:2]1[C:10]2[S:9][N:8]=[N:7][C:6]=2[CH:5]=[C:4](I)[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[Br:1][C:2]1[C:10]2[S:9][N:8]=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([F:12])[CH:18]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27339863-Fluorophenylboronic acidHCID 667608087-Bromo-5-iodo-1,2,3-benzothiadiazole

Product 1

HCID 667601397-Bromo-5-(3-fluorophenyl)-1,2,3-benzothiadiazoleYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-bromo-5-iodo-1,2,3-benzothiadiazole (20 mg, 0.0586 mmol), 3-fluorophenylboronic acid (9.85 mg, 0.0704 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane complex (2.14 mg, 0.00293 mmol), potassium carbonate (24.3 mg, 0.176 mmol) and 4:1 1,4-dioxane:water (3 mL) was heated to 60° C. for 2 h. The solution was concentrated. Purification by ISCO chromatography (1 to 3% EtOAc:heptane) afforded 15 mg (83%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.13-7.21 (m, 1 H), 7.39 (dt, J=9.7, 2.0 Hz, 1 H), 7.45-7.55 (m, 2 H), 8.04 (d, J=1.5 Hz, 1 H), 8.74 (d, J=1.3 Hz, 1 H).

Workup

  1. concentrationThe solution was concentrated
  2. customPurification by ISCO chromatography (1 to 3% EtOAc:heptane)

Sources & evidence

ORD record
ord-2dd4c3dec42649e89ae3cee2fe017789
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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