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

HRID 1851162Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[CH:6][N:5]2[N:16]=[C:17]([CH3:19])[N:18]=[C:4]2[N:3]=1.[CH:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].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:15][C:9]1[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=1[C:7]1[C:2]([C:25]2[CH:26]=[CH:27][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=2)=[N:3][C:4]2[N:5]([N:16]=[C:17]([CH3:19])[N:18]=2)[CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 1 g (3.56 mmol) of the 5-chloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine described in step 3 and 587.6 mg (3.9 mmol) 4-formylphenylboronic acid in 12 mL 1,2-dimethoxyethane are added 131 mg (0.16 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and 6.9 mL of a sodium carbonate solution (10%). The resulting mixture is heated to 90° C. under an inert gas atmosphere for 2 h. 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; the solvent is evaporated and the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield 1.01 g (77%) of the desired aldehyde.

Workup

extractionextracted three times with dichloromethane
washThe combined organic layers are washed with brine
dry with materialdried over sodium sulphate
customthe solvent is evaporated
customthe residue is purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record: ord-7a942d27fe7d4ef78d18a285a301eace
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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