Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-((4,6-Difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone
Reaction equation
ClC1C=CC2N(C(CC3C(F)=C4C(=CC=3F)N(C)N=C4)=CN=2)N=1.C([Sn](CCCC)(CCCC)C(OCC)=C)CCC.[F:42][C:43]1[C:51]([CH:52]([C:54]2[N:58]3[N:59]=[C:60]([C:63](=[O:65])[CH3:64])[CH:61]=[CH:62][C:57]3=[N:56][CH:55]=2)C)=[C:50]([F:66])[CH:49]=[C:48]2[C:44]=1[CH:45]=[N:46][N:47]2[CH3:67]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:42][C:43]1[C:51]([CH2:52][C:54]2[N:58]3[N:59]=[C:60]([C:63](=[O:65])[CH3:64])[CH:61]=[CH:62][C:57]3=[N:56][CH:55]=2)=[C:50]([F:66])[CH:49]=[C:48]2[C:44]=1[CH:45]=[N:46][N:47]2[CH3:67]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound as a light yellow solid (350 mg, 0.769 mmol, 71.3%) was synthesized from 6-chloro-3-((4,6-difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine (360 mg, 1.079 mmol), tributyl(1-ethoxyvinyl)stannane (1.095 ml, 3.24 mmol) and tetrakis-(triphenylphosphine)-palladium (374 mg, 0.324 mmol) using the same procedure as described in the synthesis of compound 31.4. 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.09 (s, 1H), 8.07 (s, 1H), 7.78 (d, 1H), 7.71 (s, 1H), 7.26 (d, 1H), 4.59 (s, 2H), 4.02 (s, 3H), 2.74 (s, 3H). LCMS (method B): [MH]+=342.0, tR=2.39 min.
Sources & evidence
- ORD record
- ord-decf84b8f1e64b18b7529e59d1ffa4a7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497368B2
Reaction notes
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