Potassium Iodide → HCID 57625531, compound

HRID 2390459Notes

Reaction equation

HRID 2390459 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13]Cl)[N:6]=[CH:5]2.[I-].[K+].C([O-])([O-])=O.[K+].[K+].[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[N:6]=[CH:5]2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 57625497HCID 57625497, compound

Product 1

HCID 57625531HCID 57625531, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-bromo-1-(3-chloropropyl)-1H-indazole (2.14 g, 7.84 mmol) in DMF (40 mL) was added potassium iodide (1.3 mg, 7.8 mmol) and K2CO3 (5.40 g, 39.2 mmol) under N2 (g). Then pyrrolidine (17.2 ml, 26.6 mmol) was added. The reaction was heated to 50° C. for 20 h. The reaction was diluted with EtOAc (100 mL) and washed with a 5% LiCl solution (4×). The organics were dried (Na2SO4), filtered, and concentrated to give the title compound (2.48 g, quant.) as a brown oil: 1H NMR (300 MHz, CDCl3) δ 7.93 (s, 1H), 7.85 (d, J=1.2 Hz, 1H), 7.45-7.41 (dd, J=8.9, 1.7 Hz, 1H), 7.36 (d, J=8.9 Hz, 1H), 4.45 (t, J=6.7 Hz, 1H), 2.44-2.36 (m, 6H), 2.15-2.07 (m, 2H), 1.78-1.74 (m, 4H); ESI MS m/z 308 [M+H]+.

Workup

  1. washwashed with a 5% LiCl solution (4×)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fa592954582845cd83aa1a9d4cc5c507
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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