Sodium Carbonate → HCID 86630690, compound

HRID 1915596Notes

Reaction equation

HRID 1915596 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 are 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 is 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) is added and the mixture is heated to 80° C. for 2 h. The work up is 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 are dried over sodium sulphate and the solvent is evaporated. The solid residue is stirred in diethylether, filtered and dried to yield the desired product.

Workup

  1. temperaturethe mixture is 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 are dried over sodium sulphate
  5. customthe solvent is evaporated
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-7d519c77287e4bcb9147dfb8806ffdf8
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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