Triphenylphosphine → 3-(2-Formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzonitrile

HRID 718617Notes

Reaction equation

HRID 718617 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH:16]=[O:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.Br[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23].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]>[CH:16]([C:14]1[N:15]=[C:8]2[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:12][CH:11]=[N:10][N:9]2[C:13]=1[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23])=[O:17]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 233813-BromobenzonitrileHCID 517044Potassium AcetateHCID 1177286388-Morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde

Product 1

HCID 1177285223-(2-Formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Using the procedure described in Example 20, Step A, compound 33a was prepared from compound 5e (232 mg, 1.00 mmol), 3-bromobenzonitrile (273 mg, 1.50 mmol), Pd(OAc)2 (15.7 mg, 0.0700 mmol), PPh3 (18.4 mg, 0.0700 mmol), and KOAc (294 mg, 3.00 mmol) in DMA (4 mL) at 110° C. for 16 h. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.14 (s, 1H), 8.13-8.17 (m, 1H), 8.10 (d, J=5.6 Hz, 1H), 8.03 (dt, J=8.0, 1.3 Hz, 1H), 7.76 (dt, J=8.0, 1.3 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 6.18 (d, J=5.6 Hz, 1H), 4.07-4.12 (m, 4H), 3.93-3.99 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C18H16N5O2: 334.1 (M+H). Found: 334.3.

Sources & evidence

ORD record
ord-48ab4516c06742ea9134a554097f01cb
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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