Hexane → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-trifluoromethyl-thieno[3,2-b]pyridin-2-yl)-imidazo[1,2-b]pyridazine

HRID 226091Notes

Reaction equation

Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]1[N:15]2[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:14]2=[N:13][C:12]=1[CH3:26].[C:27](C(O[Na])=O)([F:30])([F:29])[F:28].CN(C=O)C.C1(C)C=CC=CC=1.CCCCCC>[Cu]I.CCOC(C)=O>[CH2:21]([CH:20]([C:19]1[C:14]2[N:15]([C:11]([C:3]3[S:4][C:5]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[C:2]=3[C:27]([F:30])([F:29])[F:28])=[C:12]([CH3:26])[N:13]=2)[N:16]=[C:17]([CH3:25])[CH:18]=1)[CH2:23][CH3:24])[CH3:22]

Participants

Conditions

Temperature: 210 °C

Procedure

90 mg of 3-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.21 mmol), 57 mg of CF3CO2Na (0.42 mmol) and 80 mg of CuI (0.42 mmol) are placed into microwave vessel with 3 ml of DMF/toluene=2/1. The vial is capped and heated at 210° C. for 60 min in microwave. The reaction mixture is applied onto silica-gel column (Hexane:AcOEt=8:1) directly to produce the tile compound. 27 mg (31%) mass spectrum (m/e): 419 (M+1); 1H-NMR (CDCl3): 8.88 (dd, 1H, J=4.9 Hz, 1.4 Hz), 8.22 (dd, 1H, J=7.8 Hz, 1.4 Hz), 7.4 (dd, 1H, J=7.8 Hz, 4.9 Hz), 6.74 (s, 1H), 3.31 (m, 1H), 2.53 (s, 3H), 2.79 (s, 3H), 1.85 (m, 4H), 0.88 (t, 6H, J=7.4 Hz).

Workup

customThe vial is capped
customto produce the tile compound

Sources & evidence

ORD record: ord-3ed179e965c64c70a68c00dceafd2c28
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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