Tetrahydrofuran → HCID 69007102, compound

HRID 1432587Notes

Reaction equation

HRID 1432587 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[N:3]=1.[CH2:10]([Li])CCC.C1COCC1.Br[C:21]1[S:25][C:24]([C:26]2[N:30]3[N:31]=[C:32]([CH3:40])[CH:33]=[C:34]([CH:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[C:29]3=[N:28][C:27]=2[CH3:41])=[C:23](C)[CH:22]=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]>[CH2:36]([CH:35]([C:34]1[C:29]2[N:30]([C:26]([C:24]3[S:25][C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([CH3:10])[N:3]=4)=[CH:9][C:23]=3[CH2:22][CH3:21])=[C:27]([CH3:41])[N:28]=2)[N:31]=[C:32]([CH3:40])[CH:33]=1)[CH2:38][CH3:39])[CH3:37]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 129548002-Bromo-6-ethylpyridineHCID 579329433-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418339Butyllithium

Product 1

HCID 69007102HCID 69007102, compoundYield 28.3%

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 31, 2-bromo-6-ethyl pyridine (0.26 g, 1.41 mmol), 1.56 M n-Bu-Li (0.94 mL, 1.47 mmol), 0.5 M ZnCl2 in THF (3.0 mL, 1.53 mmol), 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) (0.047 g, 0.064 mmol) produce the title compound (0.15 g, 0.36 mmol, 28%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.34 (t, J=7.5 Hz, 3H), 1.75-1.94 (m, 4H), 2.16 (s, 3H), 2.51 (s, 3H), 2.52 (s, 3H), 2.85 (q, J=16.2, 7.5 Hz, 2H), 3.31-3.41 (m, 1H), 6.67 (s, 1H), 7.01 (d, J=7.8 Hz, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.53 (s, 1H), 8.59 (t, J=7.8 Hz, 1H). LC/MS (m/z): calcd. for C25H30N4S (M+H)+: 419.3; found: 419.3.

Sources & evidence

ORD record
ord-bc1b66291cd34f31813941fc307a98ff
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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