Tetrahydrofuran → HCID 57932900, compound

HRID 1432589Notes

Reaction equation

HRID 1432589 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.[Br-].[S:25]1[CH:29]=[CH:28][N:27]=[C:26]1[Zn+].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:26]4[S:25][CH:29]=[CH:28][N:27]=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 178419763HCID 178419763, compound

Product 1

HCID 57932900HCID 57932900, compoundYield 70%

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 (0.46 g, 1.17 mmol), 0.5 M 2-thiazolylzinc bromide in THF (4.7 mL, 2.35 mmol) and PdCl2(dppf) (0.043 g, 0.059 mmol) furnish the title compound (0.32 g, 0.81 mmol, 70%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.76-1.94 (m, 4H), 2.18 (s, 3H), 2.52 (s, 3H), 2.53 (s, 3H), 3.31-3.40 (m, 1H), 7.70 (s, 1H), 7.27 (d, J=3.6 Hz, 1H), 7.47 (s, 1H), 7.78 (d, J=3.6 Hz, 1H). LC/MS (m/z): calcd. for C21H24N4S2 (M+H)+: 397.7; found: 397.1.

Sources & evidence

ORD record
ord-32c85c4846d34edaa88267cb18644a7c
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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