Dimethylformamide → 7-Bromo-1,2,3-benzothiadiazole-5-carbonitrile

HRID 389598Notes

Reaction equation

HRID 389598 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][N:13](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[Br:1][C:2]1[C:10]2[S:9][N:8]=[N:7][C:6]=2[CH:5]=[C:4]([C:12]#[N:13])[CH:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 667608087-Bromo-5-iodo-1,2,3-benzothiadiazole

Product 1

HCID 667607867-Bromo-1,2,3-benzothiadiazole-5-carbonitrileYield 90%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 7-bromo-5-iodo-1,2,3-benzothiadiazole (22 mg, 0.0645 mmol), zinc cyanide (7.58 mg, 0.0645 mmol), Pd(PPh3)4 (7.46 mg, 0.00645 mmol) and DMF (2 mL) was heated to 60° C. for 4 h. The solution was extracted with EtOAc (50 mL), and the organic fraction was washed with saturated aqueous sodium bicarbonate solution (3×50 mL). The organic fraction was adsorbed onto silica gel and purified by ISCO chromatography (3 to 5% EtOAc:heptane) to afford 14 mg (90%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.03 (d, J=1.0 Hz, 1 H), 8.92 (d, J=1.3 Hz, 1 H).

Workup

  1. extractionThe solution was extracted with EtOAc (50 mL)
  2. washthe organic fraction was washed with saturated aqueous sodium bicarbonate solution (3×50 mL)
  3. custompurified by ISCO chromatography (3 to 5% EtOAc:heptane)

Sources & evidence

ORD record
ord-59f4c5b9954c48c3b4455d8f44406de0
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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