Sodium Carbonate → 4-[6-(Dimethylamino)-4-phenylpyridazin-3-yl]benzaldehyde

HRID 1674666Notes

Reaction equation

[CH3:1][N:2]([CH3:16])[C:3]1[N:4]=[N:5][C:6](Cl)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[CH3:1][N:2]([CH3:16])[C:3]1[N:4]=[N:5][C:6]([C:22]2[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

N,N-dimethyl 6-chloro-5-phenylpyridazin-3-amine (1-2; 120 mg, 0.51 mmol) was dissolved in dry dioxane (3 mL) and 4-formylphenyl boronic acid (136 mg, 0.91 mmol). 2 M aqueous Na2CO3 (0.75 mL) and palladium(0) tetrakis-triphenylphosphine (66 mg, 0.058 mmol) were then added. This mixture was degassed, the vessel sealed and heated at 110° C. for 24 hours. The cooled reaction was diluted with water and the product extracted into ethyl acetate, the extract dried over anhydrous NaSO4, filtered and evaporated. The product was purified by chromatography on silica gel and elution with a 25-65% ethyl acetate/hexane gradient to give 4-[6-(Dimethylamino)-4-phenylpyridazin-3-yl]benzaldehyde (1-3). NMR (CDCl3): δ9.98 (1H, s), 7.74 (2H, d, J=8 Hz), 7.54 (2H, d, J=8 Hz), 7.35 (3H, m), 7.19 (2H, d, J=8 Hz), 6.76 (1H, s), 3.29 (6H, s); m/e (m+1): 304.2

Workup

customThis mixture was degassed
customthe vessel sealed
customThe cooled reaction
extractionthe product extracted into ethyl acetate
dry with materialthe extract dried over anhydrous NaSO4
filtrationfiltered
customevaporated
customThe product was purified by chromatography on silica gel and elution with a 25-65% ethyl acetate/hexane gradient

Sources & evidence

ORD record: ord-4b7b4c84046d44f7a71207981a740321
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003643B2

Reaction notes

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