Bromopropylmagnesium → 4-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-heptan-4-ol

HRID 226117

Reaction equation

HRID 226117 reaction equation
[CH3:1][CH2:2][CH2-:3].[Mg+2].[Br-].[F:6][C:7]1[CH:32]=[CH:31][C:10]2[S:11][C:12]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([C:24](=[O:28])[CH2:25][CH2:26][CH3:27])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:13]([CH3:14])[C:9]=2[CH:8]=1>C1COCC1>[F:6][C:7]1[CH:32]=[CH:31][C:10]2[S:11][C:12]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([C:24]([OH:28])([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:13]([CH3:14])[C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 101916BromopropylmagnesiumHCID 688590651-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one

Product 1

HCID 577526054-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-heptan-4-olYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Propylmagnesium bromide (0.601 g, 4.09 mmol) is added dropwise to a solution of 1-[3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one (1.08 g, 2.72 mmol) in THF (27 mL) at 0° C. The reaction is stirred at room temperature overnight. The mixture is quenched with ammonium chloride, extracted with ethylacetate, dried over sodium sulfate, filtered, and concentrated to dryness. The crude is purified by ISCO (5% EtOAc/Hexane) to give the title compound (280 mg, 24%). 1H NMR (CDCl3): δ 7.8 (dd, J=4.8, 8.5 Hz, 1H), 7.5 (dd, J=2.5, 9.7 Hz, 1H), 7.2 (m, 1H), 6.7 (s, 1H), 6.4 (s, 1H), 2.6 (s, 3H), 2.5 (s, 3H), 2.3 (s, 3H), 2.0 (m, 3H), 1.5 (m, 1H), 1.3 (m, 4H), 0.9 (t, J=7.3, 6H) ppm. Mass spectrum (m/e): 426 (M+1).

Workup

  1. customThe mixture is quenched with ammonium chloride
  2. extractionextracted with ethylacetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude is purified by ISCO (5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-8293ec1e86804ceb9c52eb4835f4370c
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Linked notes

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