Sodium Carbonate → 4-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde

HRID 1851165Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][N:5]2[N:15]=[C:16]([CH3:18])[N:17]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([C:24]3[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=3)=[N:3][C:4]3[N:5]([N:15]=[C:16]([CH3:18])[N:17]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 0.73 g (2.8 mmol) 5-chloro-6-(3-fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 458.3 mg (3.1 mmol) 4-formylphenylboronic acid in 14 mL 1,2-dimethoxyethane are added 5.2 mL of a sodium carbonate solution (10%) and 102 mg (0.13 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture is heated to 90° C. under an inert gas atmosphere over night. The reaction mixture is diluted with water and extracted three times with dichloromethane. The combined organic layers are washed with brine and dried over sodium sulphate. After evaporation of the solvent the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield 0.85 g (87.3%) of the desired aldehyde.

Workup

extractionextracted three times with dichloromethane
washThe combined organic layers are washed with brine
dry with materialdried over sodium sulphate
customAfter evaporation of the solvent the residue
customis purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record: ord-407df0aba34843ff99af2e2d4a3a7710
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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