1H-Pyrazole, 1-methyl- → HCID 57933026, compound

HRID 1432582Notes

Reaction equation

HRID 1432582 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.C([Li])CCC.Br[C:13]1[S:17][C:16]([C:18]2[N:22]3[N:23]=[C:24]([CH3:32])[CH:25]=[C:26]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C:21]3=[N:20][C:19]=2[CH3:33])=[C:15]([CH3:34])[CH:14]=1>[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]>[CH2:28]([CH:27]([C:26]1[C:21]2[N:22]([C:18]([C:16]3[S:17][C:13]([C:6]4[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=4)=[CH:14][C:15]=3[CH3:34])=[C:19]([CH3:33])[N:20]=2)[N:23]=[C:24]([CH3:32])[CH:25]=1)[CH2:30][CH3:31])[CH3:29]

Participants

6

Reactant 3

HCID 702551H-Pyrazole, 1-methyl-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 57933026HCID 57933026, compoundYield 88%

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, 1-methylpyrazole (0.17 g, 2.04 mmol), 1.56 M n-Bu-Li (1.34 mL, 2.09 mmol), ZnCl2 (4.3 mL, 2.14 mmol), 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 1.02 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.35 g, 0.89 mmol, 88%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.17 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 3.28-3.38 (m, 1H), 4.05 (s, 3H), 6.42 (d, J=1.8 Hz, 1H), 6.68 (s, 1H), 7.08 (s, 1H), 7.46 (d, J=1.8 Hz, 1H). LC/MS (m/z): calcd. for C22H27N5S (M+H)+: 394.7; found: 394.2.

Sources & evidence

ORD record
ord-aa0a99bbe16d428fb0dbe1c0709233f7
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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