1,2-Dimethoxyethane → HCID 58579957, compound

HRID 389275Notes

Reaction equation

HRID 389275 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:10][C:11]1[C:12](Cl)=[N:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:25][C:26](=[O:45])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+].COCCOC>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.O>[CH2:23]([O:25][C:26](=[O:45])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([C:12]2[C:11]([CH2:10][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])[CH2:8][CH3:9])=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:29]=1)[CH3:24]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 58120060[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl esterHCID 58579962HCID 58579962, compound

Product 1

HCID 58579957HCID 58579957, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

(2-Chloro-quinolin-3-ylmethyl)-ethyl-carbamic acid tert-butyl ester (1.0 g, 3.11 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (1.07 g, 3.34 mmol), potassium carbonate (1.08 g, 7.8 mmol), and catalytic tetrakis(triphenylphosphine)palladium(0) were combined in 2:1 DME:H2O (18 mL), and stirred at 80° C. for 6 hours. After standard work-up, the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. customAfter standard work-up, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-511c47dc0f70496694db2c465c41187f
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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