Potassium Phosphate, Tribasic → HCID 118113216, compound

HRID 1485062Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH:17]1(B(O)O)[CH2:19][CH2:18]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH:17]1([C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=3)=[N:6][CH:7]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the compound (5.00 g) obtained in step (1) above, cyclopropylboronic acid (2.01 g), palladium(II) acetate (201 mg), tripotassium phosphate (13.4 g), tricyclohexylphosphine (0.6 mol/L, solution in toluene, 30.0 mL), toluene (95.0 mL) and water (5.0 mL) was stirred at 100° C. for 3 hours. After cooling the reaction mixture to room temperature, water was added to it and two extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter the crude product was adsorbed on diatomaceous earth, with the solvents being distilled off under reduced pressure. The crude product adsorbed on the diatomaceous earth was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-63:37) to give the titled compound as a yellow oil (3.89 g).

Workup

temperatureAfter cooling the reaction mixture to room temperature
washThe combined organic layers were washed with saturated brine
distillationbeing distilled off under reduced pressure
customwas purified by silica gel column chromatography (hexane:ethyl acetate=95:5-63:37)

Sources & evidence

ORD record: ord-0c27bbc7d1354c5aa9375e55ce5844cd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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