Ethanol → 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile

HRID 1037523Notes

Reaction equation

HRID 1037523 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]#[N:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N+:9]2[O-])=[CH:4][CH:3]=1.P(Cl)(Cl)Cl.C(O)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]#[N:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24387Phosphorus trichlorideHCID 67512786HCID 67512786, compound

Product 1

HCID 675140672-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrileYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of compound (v) (4.1 g, 0.010 mol) in chloroform (40 mL) was added phosphorus trichloride (4.1 mL, 0.047 mol) and the reaction mixture was heated to 60° C. for 1 h (monitored by TLC and LCMS). The reaction mixture was quenched in ice water and the product was extracted into DCM (2×80 mL). Concentration of solvent gave the crude product, to which was added ethanol and filtered to give 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile (vi) (3.3 g, 84%).

Workup

  1. customThe reaction mixture was quenched in ice water
  2. extractionthe product was extracted into DCM (2×80 mL)
  3. customConcentration of solvent gave the crude product
  4. filtrationfiltered

Sources & evidence

ORD record
ord-51144920e8be4cbebe0525f576318721
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

Loading…