3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine → HCID 57932983, compound

HRID 1432591Notes

Reaction equation

HRID 1432591 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.[CH2:24]([Li])[CH2:25][CH2:26][CH3:27]>[Cl-].[Cl-].[Zn+2].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]>[CH2:24]([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)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 579329433-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418339Butyllithium

Product 1

HCID 57932983HCID 57932983, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Using a procedure similar to Example 25 from 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 0.1.02 mmol), 1.34 M n-Bu-Li (1.60 mL, 2.14 mmol), 0.5 M ZnCl2 (4.3 mL, 2.14 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnishes the title compound (0.25 g, 0.69 mmol, 68%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 0.97 (t, J=7.5 Hz, 3H), 1.40-1.51 (m, 2H), 1.67-1.92 (m, 6H), 2.07 (s, 3H), 2.46 (s, 3H), 2.51 (s, 3H), 2.83 (t, J=8.0 Hz, 2H), 3.30-3.38 (m, 1H), 6.64 (s, 1H), 6.70 (s, 1H) LC/MS (m/z): calcd. for C22H31N3S (M+H)+: 370.3; found: 370.2.

Sources & evidence

ORD record
ord-e75cb446fa09412aba0f5862eb50f356
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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