Iodine → HCID 178509487, compound

HRID 246594Notes

Reaction equation

HRID 246594 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[N:2]1.[OH-].[K+].[I:14]I.S([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[I:14][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 4225291H-indazole-6-carbonitrile

Product 1

HCID 178509487HCID 178509487, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 1H-indazole-6-carbonitrile (4.5 g, 31.4 mmol) and KOH (5.3 g, 94.2 mmol) in DMSO (50 mL), was added iodine (15.9 g, 62.8 mmol) portion-wise over 10 minutes at 0° C. under ice-water bath. The final mixture was stirred for additional 2 hours at room temperature. The mixture was added slowly into saturated sodium sulfite (300 mL), the formed solid was stirred for 10 minutes, filtered, washed with saturated sodium sulfite (2×50 mL), water (2×20 mL) and dried, giving 3-iodo-1H-indazole-6-carbonitrile light as yellow solid (8.1 g, yield 95.6%). MS: (M+H)+=411; 1H NMR (300 MHz, CDCl3): δ 8.41 (s, 1H), 8.33 (s, 1H), 7.80 (s, 1H), 6.20 (s, 2H), 1.52 (s, 9H), 1.15 (s, 9H).

Workup

  1. filtrationfiltered
  2. washwashed with saturated sodium sulfite (2×50 mL), water (2×20 mL)
  3. customdried

Sources & evidence

ORD record
ord-1f58d07780264c4ea5d082e1cb5c86d6
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…