Tetrahydrofuran → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-5-phenyl-thiophen-2-yl)-imidazo[1,2-b]pyridazine

HRID 1432584Notes

Reaction equation

HRID 1432584 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.[I-].[C:25]1([Zn+])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1COCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:17]([CH:16]([C:15]1[C:10]2[N:11]([C:7]([C:5]3[S:6][C:2]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[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

5

Reactant 3

HCID 8028TetrahydrofuranHCID 579329433-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178506617HCID 178506617, compound

Product 1

HCID 579329588-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-5-phenyl-thiophen-2-yl)-imidazo[1,2-b]pyridazineYield 50%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Using a procedure similar to Example 32, 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.50 g, 1.27 mmol) and PdCl2(dppf) (0.05 g, 0.069 mmol) and 0.5 M solution of phenylzinc iodide in THF (5.5 mL, 2.76 mmol) furnish the title compound (0.25 g, 0.64 mmol, 50%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.76-1.94 (m, 4H), 2.17 (s, 3H), 2.52 (s, 3H), 2.53 (s, 3H), 3.31-3.41 (m, 1H), 6.68 (s, 1H), 7.26 (s, 1H), 7.27-30 (m, 1H), 7.35-7.41 (m, 2H), 7.61-7.66 (m, 2H). LC/MS (m/z): calcd. for C24H27N3S (M+H)+: 390.3; found: 390.3.

Sources & evidence

ORD record
ord-169522005e3f45a68d311be35f62151e
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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