Potassium Phosphate, Tribasic → Tert-butyl 2-(3-nitro-5-(pyridin-4-yl)phenyl)acetate

HRID 1628298Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C(O)(CC)(C)C.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]>[N+:8]([C:6]1[CH:5]=[C:4]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:3]=[C:2]([C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)[CH:7]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 2-(3-chloro-5-nitrophenyl)acetate 52.B (2.00 g, 7.36 mmol) and pyridin-4-ylboronic acid (1.09 g, 8.83 mmol) in t-amyl alcohol (20 mL) was added K3PO4 (4.69 g, 22.1 mmol), Pd2(dba)3 (337 mg, 0.368 mmol) and XPhos (702 mg, 1.47 mmol). The mixture was stirred for 3 hours at 100° C. and then was filtered over Celite. The liquid phase was concentrated and partitioned between water and AcOEt. The organic phase was then washed with brine, dried over MgSO4, concentrated and purified by flash chromatography on silica gel to afford tert-butyl 2-(3-nitro-5-(pyridin-4-yl)phenyl)acetate 52.0 (2.03 g, 72% yield).

Workup

filtrationwas filtered over Celite
concentrationThe liquid phase was concentrated
custompartitioned between water and AcOEt
washThe organic phase was then washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
custompurified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-b6a9a1f272994e0ca281fd1551f77db8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

Loading…