Diisopropylethylamine → HCID 70559180, compound

HRID 570980Notes

Reaction equation

HRID 570980 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)#[CH:13].C(N(C(C)C)CC)(C)C>CN(C=O)C.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.[Cu]I>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[C:14]([C:12]#[C:13][C:2]2[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:15]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 19652933-ethynylquinolineHCID 16217886Methyl 6-bromopyridine-2-carboxylate

Product 1

HCID 70559180HCID 70559180, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 6-bromo-2-pyridinecarboxylate (0.3 g, 1.3 mmol), 3-ethynylquinoline (0.3 g, 1.3 mmol), Pd(PPh3)4 (0.11 g, 0.01 mmol), CuI (0.179 g, 0.1 mmol) and diisopropylethylamine (0.5 ml, 3 mmol) in DMF (15 ml) was stirred at ambient temperature for 12 hrs under an atmosphere of nitrogen. The reaction mixture was concentrated and the crude product was purified by flash chromatography on silica gel (elution with 10% ethyl acetate in n-hexane) to provide methyl 6-[(quinolin-3-yl)ethynyl]pyridine-2-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by flash chromatography on silica gel (elution with 10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-0a1c19d5ce77470b8733fe00220def87
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

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