Sodium Carbonate → 4-(7-Methoxy-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

HRID 1851201Notes

Reaction equation

HRID 1851201 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([O:14][CH3:15])[N:5]2[N:16]=[CH:17][CH:18]=[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.ClCCl.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]>[CH3:15][O:14][C:6]1[N:5]2[N:16]=[CH:17][CH:18]=[C:4]2[N:3]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 866306725-Chloro-7-methoxy-6-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 866306734-(7-Methoxy-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1.00 g 5-chloro-7-methoxy-6-phenylpyrazolo[1,5-a]pyrimidine and 0.69 g 4-formylphenylboronic acid in 20 mL 1,2-dimethoxyethane were added 7.3 mL of a 10% w/w sodium carbonate solution and 0.14 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The mixture was heated for 45 min under microwave irradiation to 120° C. This mixture was worked up by diluting with water and extraction with dichloromethane. The organic layers were dried over Na2SO4 and concentrated to yield the crude product, which was purified by chromatography on silica gel (methanol/dichloromethane).

Workup

  1. dry with materialThe organic layers were dried over Na2SO4
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0490ca0a883c464b8c407c0bcdcf6561
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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