Ethanol → HCID 86722004, compound

HRID 1398040Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:31].[Na+].[Na+].CCO.[C:39]1([CH3:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]=[C:10]([C:41]3[CH2:40][C@H:39]([CH3:45])[O:31][C@@H:43]([CH3:44])[CH:42]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A flask is charged with 5-(4-chlorophenyl)-1-(2-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.10 g, 3.70 mmol), trans-2,6-dimethyl-3,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate (1.06 g, 4.07 mmol), Pd(PPh3)4 (0.24 g, 5 mol %), 2 M Na2CO3 (16 mL), EtOH (16 mL) and toluene (32 mL) and heated at 80° C. for 6 h. The reaction was diluted with EtOAc (100 mL) and washed with saturated aqueous NaHCO3 (2×100 mL) and brine (100 mL), and the organic layer dried over Na2SO4 and evaporated. The crude product was purified by silica gel chromatography (Thomson Scientific 25-g cartridge, 10-100% EtOAc/heptane in 10 column volumes) to give 0.68 g (66%) of the title compound as a white solid.

Workup

washwashed with saturated aqueous NaHCO3 (2×100 mL) and brine (100 mL)
dry with materialthe organic layer dried over Na2SO4
customevaporated
customThe crude product was purified by silica gel chromatography (Thomson Scientific 25-g cartridge, 10-100% EtOAc/heptane in 10 column volumes)

Sources & evidence

ORD record: ord-44d257056ed842b4b55d33b322164058
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901314B2

Reaction notes

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