Potassium Acetate → HCID 57932915, compound

HRID 1432708Notes

Reaction equation

HRID 1432708 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:13]=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].Br[C:18]1[S:22][C:21]([C:23]2[N:27]([CH2:28][C:29]([F:32])([F:31])[F:30])[N:26]=[CH:25][N:24]=2)=[CH:20][C:19]=1[Cl:33].CC([O-])=O.[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].C(OP(OCC(Br)CBr)(OCC(Br)CBr)=O)C(Br)CBr.CN1C(=O)CCC1>[Cl:33][C:19]1[CH:20]=[C:21]([C:23]2[N:27]([CH2:28][C:29]([F:31])([F:30])[F:32])[N:26]=[CH:25][N:24]=2)[S:22][C:18]=1[C:13]1[N:8]2[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]2=[N:15][C:14]=1[CH3:16]

Participants

8

Reactant 3

HCID 517044Potassium AcetateHCID 68840689HCID 68840689, compoundHCID 688412672,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

Product 1

HCID 57932915HCID 57932915, compoundYield 78.1%

Reagents, catalysts & solvents 4

HCID 31356Tris(2,3-dibromopropyl) PhosphateCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using a procedure analogous to Example 231, 8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.25 g, 1.14 mmol), 5-(5-bromo-4-chloro-thiophen-2-yl)-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazole (0.47 g, 1.37 mmol), KOAc (0.56 g, 5.60 mmol), TBABr (0.37 g, 1.14 mmol), and NMP (3 mL), Pd(OAc)2 (0.013 g, 0.057 mmol) and TDBPP (0.037 g, 0.057 mmol) furnish the title compound (0.43 g, 0.89 mmol, 78%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 1.75-1.92 (m, 4H), 2.52 (s, 3H), 2.53 (s, 3H), 3.27-3.36 (m, 1H), 4.98 (q, J=15.7, 7.9 Hz, 2H), 6.74 (s, 1H), 7.45 (s, 1H), 8.03 (s, 1H). LC/MS (m/z): calcd. for C21H22ClF3N6S (M+H)+: 483.1; found: 483.2.

Sources & evidence

ORD record
ord-dfc70adc4d1444fd9119936091534d0a
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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