1,2-Dimethoxyethane → HCID 66921635, compound

HRID 1364307Notes

Reaction equation

HRID 1364307 reaction equation
Br[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[C:14]([O-])([O-])=O.[K+].[K+].CO[CH2:22][CH2:23]OC>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>[CH2:13]([O:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH:22]=[CH2:23])[CH:3]=[CH:4][N:5]=2)[N:10]=1)[CH3:14]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 534216178-Bromo-2-methoxy-1,5-naphthyridine

Product 1

HCID 66921635HCID 66921635, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

A suspension of 8-bromo-2-methoxy-[1,5]naphthyridine (1.2 g, 5 mmol), tetrakis(triphenylphosphine)palladium (0.29 g), K2CO3 (0.691 g) and 2,4,6-trivinyl-cyclotriboroxane pyridine complex (1.2 g, prepared according to J. Org. Chem. (2002), 67, 4969) in DME (40 mL) and water (12 mL) was heated at 85° C. under N2 overnight. The mixture was cooled to rt, diluted with water and extracted with ether. The combined org. extracts were dried over MgSO4 and concentrated in vacuo. The product (1 g of red oil) was used as such without further purification.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with ether
  3. dry with materialextracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customsuch without further purification

Sources & evidence

ORD record
ord-bd68ac69e08a469385fb69ba1747000c
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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