HCID 13220427, compound → HCID 57752687, compound

HRID 226078Notes

Reaction equation

[Cl:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.[Li]CCCC.[CH2:16]([CH:18]([C:21]1[C:22]2[N:23]([C:28](I)=[C:29]([CH3:31])[N:30]=2)[N:24]=[C:25]([CH3:27])[CH:26]=1)[CH2:19][CH3:20])[CH3:17]>C1COCC1.[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]>[Cl:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:28]1[N:23]2[N:24]=[C:25]([CH3:27])[CH:26]=[C:21]([CH:18]([CH2:16][CH3:17])[CH2:19][CH3:20])[C:22]2=[N:30][C:29]=1[CH3:31]

Participants

Conditions

Temperature: -78 °C

Procedure

80 mg of 3-Chloro-thieno[3,2-b]pyridine (0.47 mmol) is dissolved in 3.0 ml of dry THF and cooled to −78° C. 0.19 ml of n-BuLi (0.47 mmol) is added slowly and stirred at −78° C. for 10 min. 0.94 ml of 0.5M ZnCl2 in THF (0.47 mmol) is added at −78° C. and stirred at room temperature for 10 min. 161 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.47 mmol) and 22 mg of PdCl2(dppf) (0.03 mmol) are added and the vial is capped with a Teflon cap and heated at 80° C. overnight. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt:2M NH3 in MeOH=20:4:1) to give 84 mg of the title compound (47%). mass spectrum (m/e): 385; 1H-NMR (CDCl3): 8.84 (d, 1H, J=4.7 Hz), 8.20 (d, 1H, J=8.3 Hz), 7.38 (dd, 1H, J=4.7 Hz, 8.3 Hz), 6.76 (s, 1H), 3.34 (m, 1H), 2.56 (s, 3H), 2.52 (s, 3H), 1.85 (m, 4H), 0.89 (t, 6H, J=7.4 Hz) ppm.

Workup

stirringstirred at room temperature for 10 min
customcap
temperatureheated at 80° C. overnight
concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record: ord-cc99bc1f4806429f8354b6b48d86fd19
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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