7-Bromo-5-iodo-1,2,3-benzothiadiazole → 7-Bromo-5-methyl-1,2,3-benzothiadiazole

HRID 389602Notes

Reaction equation

HRID 389602 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.[CH3:12][Zn]C>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.O1CCOCC1>[Br:1][C:2]1[C:10]2[S:9][N:8]=[N:7][C:6]=2[CH:5]=[C:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 2

HCID 667608087-Bromo-5-iodo-1,2,3-benzothiadiazoleHCID 178477796HCID 178477796, compound

Product 1

HCID 667608807-Bromo-5-methyl-1,2,3-benzothiadiazoleYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-bromo-5-iodo-1,2,3-benzothiadiazole (30 mg, 0.088 mmol), Pd(PPh3)4 (10.2 mg, 0.0088 mmol) and 1,4-dioxane (5 mL) was added dimethylzinc (2 M in toluene, 0.1 mL, 0.210 mmol), and the reaction was heated to 50° C. for 3 h. The solution was quenched with MeOH (1 mL), adsorbed onto silica gel, and purified by ISCO chromatography (1 to 3% EtOAc:heptane) to afford 12 mg (60%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.52 (s, 3 H), 7.58 (s, 1 H), 8.27 (s, 1 H).

Workup

  1. customThe solution was quenched with MeOH (1 mL)
  2. custompurified by ISCO chromatography (1 to 3% EtOAc:heptane)

Sources & evidence

ORD record
ord-2914a7f423d943e0898cee5217a0e1ae
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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