1-Bromo-3-chloropropane → HCID 57625497, compound

HRID 2390458Notes

Reaction equation

HRID 2390458 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.Br[CH2:12][CH2:13][CH2:14][Cl:15].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:12][CH2:13][CH2:14][Cl:15])[N:6]=[CH:5]2

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 7619295-bromo-1H-indazole

Product 1

HCID 57625497HCID 57625497, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-1H-indazole (3.0 g, 15 mmol) in DMSO (15 mL) was added 1-bromo-3-chloropropane (2.0 mL, 20 mmol) and K2CO3 (6.33 g, 45.9 mmol). The reaction was stirred at room temperature for 72 h; then the reaction was diluted with methylene chloride (100 mL) and washed with a 5% LiCl solution (4×). The organics were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (40 g ISCO column, hexanes/EtOAc, 95:5 to 65:35) gave the title compound (2.14 g, 51%) as a white powder: 1H NMR (500 MHz, CDCl3) δ 7.95 (d, J=0.5, 1H), 7.87 (d, J=1.5 Hz, 1H), 7.48-7.45 (dd, J=8.9, 1.8 Hz, 1H), 7.38 (d, J=8.9 Hz, 1H), 4.54 (t, J=6.4 Hz, 2H) 3.47 (t, J=6.0 Hz, 2H) 2.42-2.37 (m, 2H); ESI MS m/z 273 [M+H]+.

Workup

  1. washwashed with a 5% LiCl solution (4×)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (40 g ISCO column, hexanes/EtOAc, 95:5 to 65:35)

Sources & evidence

ORD record
ord-bf25ae713da64fb6ba531516301584e5
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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