Dimethylformamide → HCID 10472300, compound

HRID 1828850Notes

Reaction equation

HRID 1828850 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:23](=[CH:24][CH:25]=1)[C:7]1[NH:8][N:9]=[C:10]([C:11]3[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:13][O:14][C:15]=3[CH3:16])[C:6]=1[CH2:5]2.BrC1C=C2C(=CC=1)CCC2.[CH3:36][N:37](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH3:16][C:15]1[O:14][N:13]=[C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]=1[C:10]1[NH:9][N:8]=[C:7]2[C:23]3[C:4]([CH2:5][C:6]=12)=[CH:3][C:2]([C:36]#[N:37])=[CH:25][CH:24]=3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2671395-bromo-2,3-dihydro-1H-indeneHCID 178434983HCID 178434983, compound

Product 1

HCID 10472300HCID 10472300, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
80 °C

Procedure

A suspension of 6-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-1,4-dihydroindeno[1,2-c]pyrazole (500 mg, 1.3 mmol) (prepared from 5-bromoindane in the same manner as Example 1) and zinc cyanide (912 mg, 7.8 mmol) in DMF (5 ml) was degassed with N2 for 0.5 hr, tetrakis(triphenylphosphine)palladium(0) (100 mg) was added and heated to 80° C. for 3 days. The reaction mixture was cooled, poured into 10% ammonium hydroxide solution and extracted into EtOAc. The organic layer was washed with H2O(×3) then dried (MgSO4), evaporated and the residue chromatographed on silica, eluting with dichloromethane and recrystallised from hot dichloromethane to give the title compound as a white solid (55 mg, 13%). 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J=8.4 Hz, 1H), 7.68 (d, J=7.6 Hz, 2H), 7.51–7.37 (m, 5H), 3.35 (s, 2H), 2.59 (s, 3H), m/z (ES+) 339 (M+H)+.

Workup

  1. customwas degassed with N2 for 0.5 hr
  2. additiontetrakis(triphenylphosphine)palladium(0) (100 mg) was added
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into 10% ammonium hydroxide solution
  5. extractionextracted into EtOAc
  6. washThe organic layer was washed with H2O(×3)
  7. dry with materialthen dried (MgSO4)
  8. customevaporated
  9. customthe residue chromatographed on silica
  10. washeluting with dichloromethane
  11. customrecrystallised from hot dichloromethane

Sources & evidence

ORD record
ord-a52b34f0237546c7984a598d4c14daea
Source dataset
uspto-grants-2006_06
Patent number
US07060710B2

Reaction notes

Loading…