Sodium Bicarbonate → HCID 24809861, compound

HRID 1446161Notes

Reaction equation

[C:1]1([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[N:16][O:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=3)=[O:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][C:27]1(C)C(C)(C)OB(C=C)O1.C(=O)(O)[O-].[Na+]>COCCOC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[N:16][O:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([CH:26]=[CH2:27])=[CH:21][CH:20]=3)=[O:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-[(3-phenylpyrrolidin-1-yl)carbonyl]-5-(4-iodophenyl)isoxazole (50 mg, 0.11 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (50 μL, 0.78 mmol), sodium bicarbonate (20 mg, 0.23 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (2 mg, 0.002 mmol) in 1,2-dimethoxyethane/water (5 mL) was stirred at 60° C. for 1 h. The residue was purified on SiO2 (2:1 hexane/ethyl acetate) to afford the title compound (25 mg). HRMS (ESI, pos. ion) m/z calcd for C22H20N2O2: 344.1525, found 344.1521.

Workup

customThe residue was purified on SiO2 (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-25bf9705ea734ab4be97b126999d87db
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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