Sodium Carbonate → HCID 86630690, compound

HRID 1851215Notes

Reaction equation

HRID 1851215 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[CH:6][N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1.[CH:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].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]>[S:10]1[CH:11]=[CH:12][C:8]([C:7]2[C:2]([C:21]3[CH:22]=[CH:23][C:18]([CH:16]=[O:17])=[CH:19][CH:20]=3)=[N:3][C:4]3[N:5]([N:13]=[CH:14][CH:15]=3)[CH:6]=2)=[CH:9]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic Acid2×HCID 86630691HCID 86630691, compound

Product 1

HCID 86630690HCID 86630690, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 276 mg 5-chloro-6-thiophen-3-yl-pyrazolo[1,5-a]pyrimidine and 228 mg 4-formylphenylboronic acid in 13 mL 1,2-dimethoxyethane were added 1.8 mL of a 10% w/w sodium carbonate solution and 48 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture was heated to 80° C. under an inert gas atmosphere for 7 h. An additional portion of 228 mg 4-formylphenylboronic acid and 48 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) was added and the mixture was heated to 80° C. for 2 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The solid residue was stirred in diethylether, filtered and dried to yield the desired product.

Workup

  1. temperaturethe mixture was heated to 80° C. for 2 h
  2. customseparating
  3. extractionthe phases and extraction of the aqueous phase with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customthe solvent was evaporated
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-a2492e3ae8d9470281e444bbc63e91a4
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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