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

HRID 503757Notes

Reaction equation

HRID 503757 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 are 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 is heated for 45 min under microwave irradiation to 120° C. This mixture is worked up by diluting with water and extraction with dichloromethane. The organic layers are dried over Na2SO4 and concentrated to yield the crude product, which is purified by chromatography on silica gel (methanol/dichloromethane).

Workup

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

Sources & evidence

ORD record
ord-b49a170209cd4640b68b4d175bcd0684
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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