Dimethylformamide → HCID 11842672, compound

HRID 226041Notes

Reaction equation

HRID 226041 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[N:15]4[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:14]4=[N:13][C:12]=3[CH3:26])[NH:8]2)=[CH:4][CH:3]=1.[CH3:27]N(C=O)C.[H-].[Na+].CI>CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[N:15]4[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:21][CH3:22])[CH2:23][CH3:24])[C:14]4=[N:13][C:12]=3[CH3:26])[N:8]2[CH3:27])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136081565HCID 136081565, compound

Product 1

HCID 11842672HCID 11842672, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(6-chloro-1H-indol-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.050 g, 0.14 mmol) and DMF (2 mL) is added 60% NaH (0.013 g, 0.33 mmol). The solution is stirred for 30 minutes and MeI (0.010 mL, 0.16 mmol) is added. The solution is stirred for 1 hour, diluted with EtOAc (20 mL), washed with water (2×10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated. The residue is purified by silica gel chromatography (30%-50% EtOAc gradient) to furnish the title compound (0.021 g, 0.055 mmol, 40%). 1H NMR (CDCl3), δ 0.90 (t, J=7.4 Hz, 6H), 1.75-1.95 (m, 4H), 2.49 (s, 3H), 2.51 (s, 3H), 3.31-3.40 (m, 1H), 3.57 (s, 3H), 6.65 (d, J=0.9 Hz, 1H), 6.72 (s, 1H), 7.12 (dd, J=8.4, 1.8 Hz, 1H), 7.40-7.42 (m, 1H), 7.58 (8.4 Hz, 1H) ppm. LC/MS (m/z): calcd. for C22H25ClN4 (M+H)+: 380.2. found: 381.2.

Workup

  1. stirringThe solution is stirred for 1 hour
  2. washwashed with water (2×10 mL), brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography (30%-50% EtOAc gradient)

Sources & evidence

ORD record
ord-e4a5ab263d9745d7ae5d9447fd421b27
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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