2-Fluoropyridine-4-boronic acid → N-(6-(2-Fluoropyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162434Notes

Reaction equation

HRID 1162434 reaction equation
CC1C=CC(S([NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]4[N:22]([CH:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[N:26]=4)[N:23]=3)[CH:15]=[CH:16]C=2)(=O)=O)=CC=1.ClC1C=CC2N(C=C(NC(=O)C)N=2)N=1.[F:45]C1C=C(B(O)O)C=CN=1>>[F:45][C:12]1[CH:13]=[C:14]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([CH:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[N:26]=3)[N:23]=2)[CH:15]=[CH:16][N:11]=1

Participants

4

Reactant 3

HCID 27833962-Fluoropyridine-4-boronic acidHCID 44124523N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamideHCID 59519510N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide

Product 1

HCID 44124632N-(6-(2-Fluoropyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Procedure

Following the procedure described for N-(6-(3-(4-methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 1), N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (Example 1, Step 4) (0.040 g, 0.19 mmol) was reacted with 2-fluoropyridin-4-ylboronic acid (0.054 g, 0.38 mmol, Synthonix, Wake Forest, N.C.) to afford the title compound as a yellow solid. MS (ESI positive ion) m/z: 272 (M+1). 1H NMR (400 MHz, DMSO-d6): δ pp, 11.00 (s, 1H), 8.43 (d, J=5.3 Hz, 1H), 8.18 (d, J=10.0 Hz, 1H), 8.05 (t, J=1.6 Hz, 0.5H), 8.04 (t, J=1.6 Hz, 0.5H), 7.96 (d, J=9.4 Hz, 1H), 7.86 (s, 1H), 2.13 (s, 3H).

Sources & evidence

ORD record
ord-0384f7fb07134cbeb50a4012a274635e
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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