Dichloromethane → HCID 57932945, compound

HRID 1432692Notes

Reaction equation

HRID 1432692 reaction equation
C(Cl)Cl.[CH2:4]([CH:6]([C:9]1[C:10]2[N:11]([C:16]([C:20]3[O:21][CH:22]=[CH:23][C:24]=3[CH3:25])=[C:17]([CH3:19])[N:18]=2)[N:12]=[C:13]([CH3:15])[CH:14]=1)[CH2:7][CH3:8])[CH3:5].C1C(=O)N([Br:33])C(=O)C1>O>[Br:33][C:22]1[O:21][C:20]([C:16]2[N:11]3[N:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH:6]([CH2:7][CH3:8])[CH2:4][CH3:5])[C:10]3=[N:18][C:17]=2[CH3:19])=[C:24]([CH3:25])[CH:23]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 579329198-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-furan-2-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 57932945HCID 57932945, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A CH2Cl2 solution (4 mL) of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(3-methyl-furan-2-yl)-imidazo[1,2-b]pyridazine (32.4 mg, 0.11 mmol) is cooled to 0° C. under a CaSO4 drying tube and treated with NBS (20.1 mg, 0.11 mmol). After 15 minutes at 0° C., the mixture is warmed to room temperature. After an additional 10 minutes, the reaction mixture is poured into H2O (25 mL) and extracted into CH2Cl2 (2×25 mL). The combined organic extracts are washed with aq. brine, dried over Na2SO4, filtered, and concentrated. The crude product is purified by chromatography using hexane-ethyl acetate gradient (100% hexane to 10% ethyl acetate in hexane) to elute the title compound (26.3 mg, 64% yield) as a solid. ES-MS (m/z): calc'd for C18H22BrN3O: 375.1; found 376.2 (M+H); 1H NMR (400 mHz, CDCl3): δ 6.72 (s, 1H), 6.40 (s, 1H), 3.34 (m, 1H), 2.56 (s, 3H), 2.49 (s, 3H), 2.07 (s, 3H), 1.93-1.77 (m, 4H), 0.89 (t, J=7.5 Hz, 6H).

Workup

  1. waitAfter an additional 10 minutes
  2. extractionextracted into CH2Cl2 (2×25 mL)
  3. washThe combined organic extracts are washed with aq. brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-4a87cc97e98e451a8f133f20f5c59f3a
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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