Dimethylformamide → HCID 57932965, compound

HRID 1432577Notes

Reaction equation

HRID 1432577 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[N:11]3[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]3=[N:9][C:8]=2[CH3:22])=[C:4]([CH3:23])[CH:3]=1.[CH3:24][N:25](C=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:17]([CH:16]([C:15]1[C:10]2[N:11]([C:7]([C:5]3[S:6][C:2]([C:24]#[N:25])=[CH:3][C:4]=3[CH3:23])=[C:8]([CH3:22])[N:9]=2)[N:12]=[C:13]([CH3:21])[CH:14]=1)[CH2:19][CH3:20])[CH3:18]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 579329433-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 57932965HCID 57932965, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.50 g, 1.28 mmol), DMF (5 mL), and Zn(CN)2 (0.090 g, 0.76 mmol) is degassed with nitrogen for 15 minutes. Pd(PPh3)4 (0.74 g, 0.064 mmol) and the solution heated at 100° C. overnight. The solution is diluted with EtOAc (50 mL), washed with 2 M NH4OH (2×30 mL), brine (30 mL), dried over MgSO4, filtered and concentrated. Purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient) furnish the title compound (0.39 g, 1.15 mmol, 91%). 1H NMR (CDCl3), δ 0.87 (t, J=7.5 Hz, 6H), 1.74-1.91 (m, 4H), 2.15 (s, 3H), 2.46 (s, 3H), 2.51 (s, 3H), 3.26-3.34 (m, 1H), 6.72 (s, 1H), 7.53 (s, 1H). LC/MS (m/z): calcd. for C19H22N4S (M+H)+: 339.6; found: 339.2.

Workup

  1. washwashed with 2 M NH4OH (2×30 mL), brine (30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurified by ISCO column chromatography (15%-20% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-df439cfe1d974a9796afdd453588b3ae
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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