Triphenylphosphine → Ethyl 3-(6-cyanopyridin-3-yl)-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

HRID 718615Notes

Reaction equation

HRID 718615 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.Br[C:22]1[CH:23]=[CH:24][C:25]([C:28]#[N:29])=[N:26][CH:27]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+]>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:28]([C:25]1[N:26]=[CH:27][C:22]([C:13]2[N:9]3[N:10]=[CH:11][CH:12]=[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[C:8]3=[N:15][C:14]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:23][CH:24]=1)#[N:29]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 8171545-Bromopyridine-2-carbonitrileHCID 117728723Ethyl 8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Product 1

HCID 117728523Ethyl 3-(6-cyanopyridin-3-yl)-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Using the procedure described in Example 20, Step A, the title compound was prepared from Compound 5c (1.38 g, 5.00 mmol), 5-bromo-2-cyanopyridine (1.42 g, 7.50 mmol), Pd(OAc)2 (78.6 mg, 0.350 mmol), PPh3 (91.8 mg, 0.350 mmol), and KOAc (1.47 g, 15.0 mmol) in DMA (20 mL) at 110° C. for 16 h. 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.00 (s, 1H), 8.20 (dd, J=8.1, 1.7 Hz, 1H), 8.05 (d, J=5.6 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 6.17 (d, J=5.6 Hz, 1H), 4.36 (q, J=7.3 Hz, 2H), 4.02-4.13 (m, 4H), 3.90-3.99 (m, 4H), 1.30 (t, J=7.1 Hz, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C19H18N6O3: 379.2 (M+H). Found: 379.1.

Sources & evidence

ORD record
ord-de9e00b271d6419f953d0080a87a8683
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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