(Pyridin-4-yl)boronic acid → N-(6-(6-Chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:21]4[CH:26]=[CH:25]C=[C:23](F)[CH:22]=4)=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:28][S:29]([CH3:32])(=[O:31])=[O:30].ClC1[N:39]=CC(C2C=CC3N(C(I)=C(NC(=O)C)N=3)N=2)=CC=1NS(C)(=O)=O.N1C=CC(B(O)O)=CC=1>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:21]4[CH:22]=[CH:23][N:39]=[CH:25][CH:26]=4)=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:28][S:29]([CH3:32])(=[O:31])=[O:30]Participants
Reactant 3
Product 1
Procedure
Following the procedure described for N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (TFA salt) (Example 22), N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (0.250 g, 0.493 mmol) (Example 21) was reacted with pyridine-4-boronic acid (0.0606 g, 0.493 mmol, Boron Molecular) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane adduct (0.040 g, 0.049 mmol, Strem Chemical, Inc., Newburyport, Mass.) for 6 h at 90° C. to afford the title compound as a yellow solid (0.080 g, 28%). MS (ESI, positive ion) m/z: 458 (M−TFA+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.12 (s, 3H), 3.24 (s, 3H), 8.17 (d, J=9.6 Hz, 1H), 8.27 (d, J=6.1 Hz, 2H), 8.42 (d, J=9.4 Hz, 1H), 8.61 (d, J=2.0 Hz, 1H), 8.79 (d, J=6.1 Hz, 2H), 9.01 (d, J=2.0 Hz, 1H), 9.98 (br s, 1H), 10.76 (s, 1H).
Sources & evidence
- ORD record
- ord-ca796ad37dca4a43869e74458a59d05c
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820665B2
Reaction notes
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