Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-((4,6-Difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

HRID 1892395Notes

Reaction equation

HRID 1892395 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]CC)=[CH2:64])[CH:61]=[CH:62][C:57]3=[N:56][CH:55]=2)C)=[C:50]([F:68])[CH:49]=[C:48]2[C:44]=1[CH:45]=[N:46][N:47]2[CH3:69]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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:68])[CH:49]=[C:48]2[C:44]=1[CH:45]=[N:46][N:47]2[CH3:69]

Participants

5

Reactant 3

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 581475346-chloro-3-((4,6-difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazineHCID 581904573-[1-(4,6-Difluoro-1-methyl-1H-indazol-5-yl)-ethyl]-6-(1-ethoxy-vinyl)-imidazo[1,2-b]pyridazine

Product 1

HCID 581904931-(3-((4,6-Difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanoneYield 71.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound as a light yellow solid (350 mg, 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 Pd(PPh3)4 (374 mg, 0.324 mmol) using the same procedure as described in the synthesis of compound 51.3 and 51.4. 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-5c91536e76b14dcfa14ca1b7aadcc4a6
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

Loading…