Ethanol → 3-(3-Chloro-4-pyridin-3-yl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine, hydrochloride salt

HRID 1432666Notes

Reaction equation

HRID 1432666 reaction equation
Br[C:2]1[C:3]([Cl:23])=[C:4]([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])[S:5][CH:6]=1.I[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.CCO>[Zn].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]>[ClH:23].[ClH:23].[Cl:23][C:3]1[C:2]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:6][S:5][C:4]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]2=[N:9][C:8]=1[CH3:22]

Participants

7

Reactant 3

HCID 702EthanolHCID 707143-IodopyridineHCID 579330783-(4-Bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 2

HCID 313Hydrochloric AcidHCID 1317277213-(3-Chloro-4-pyridin-3-yl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine, hydrochloride saltYield 52.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Using a procedure analogous to Example 175, 3-(4-bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 0.97 mmol), Reike® Zn (0.5 g/mL solution in THF, 2.5 mL, 1.94 mmol), 3-iodo-pyridine (0.30 g, 1.45 mmol), PdCl2(dppf) (0.035 g, 0.048 mmol), and a 1 M solution of HCl in EtOH (0.61 mL, 0.61 mmol) furnish the title compound (0.076 g, 0.17 mmol, 18%). 1H-NMR (CDCl3), δ 0.95 (t, J=7.0 Hz, 6H), 1.71-1.88 (m, 2H), 1.88-2.01 (m, 2H), 2.68 (s, 3H), 2.81 (s, 3H), 3.85-3.96 (m, 1H), 5.28 (s, 1H), 7.27 (bs, 1H), 8.09 (bs, 1H), 8.23 (bs, 1H), 8.70 (bs, 1H), 8.89 (bs, 1H), 9.18 (bs, 1H). LC/MS (m/z): calcd. for C22H24Cl2N4S (M+H)+: 411.1; found: 411.2.

Sources & evidence

ORD record
ord-d88e559ad38b44f581c3388f929f217f
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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