Dimethylformamide → 7-Bromo-1,2-benzothiazole-6-carbonitrile

HRID 389601Notes

Reaction equation

HRID 389601 reaction equation
[Br:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1I.[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]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:12]#[N:13]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 667602837-Bromo-6-iodo-1,2-benzothiazole

Product 1

HCID 667605697-Bromo-1,2-benzothiazole-6-carbonitrileYield 50%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

A suspension of 7-bromo-6-iodo-1,2-benzothiazole (43.2 mg, 0.127 mmol), zinc cyanide (13.6 mg, 0.116 mmol), and Pd(PPh3)4 (15.9 mg, 0.0138 mmol) in DMF (1.6 mL) was heated to 80° C. in a microwave for 15 min. The reaction mixture was concentrated in vacuo. Purification of the residue by ISCO chromatography (20 to 100% dichloromethane:heptane) to afford 16.4 mg (50%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.25 (s, 1H), 7.77 (d, J=7.58 Hz, 1H), 7.69 (d, J=8.08 Hz, 1H); MS (ESI): 237.15, 239.14 [M−H]+; HPLC tR=0.90 min (HPLC: nonpolar—2 min).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification of the residue by ISCO chromatography (20 to 100% dichloromethane:heptane)

Sources & evidence

ORD record
ord-5f9fff2354ae41c0b6a350be77e2fdf7
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…