Triethylamine → Methyl 4-(5-(1,3-dioxoisoindolin-2-yl)pent-1-ynyl)-2-methoxynicotinate

HRID 1034939Notes

Reaction equation

HRID 1034939 reaction equation
I[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH3:13])[N:5]=[CH:4][CH:3]=1.[CH2:14]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])[CH2:15][CH2:16][C:17]#[CH:18].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[CH2:14][CH2:15][CH2:16][C:17]#[C:18][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH3:13])[N:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 11769822N-(4-Pentynyl)phthalimideHCID 58819970Methyl 4-iodo-2-methoxynicotinate

Product 1

HCID 58094505Methyl 4-(5-(1,3-dioxoisoindolin-2-yl)pent-1-ynyl)-2-methoxynicotinate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 4-iodo-2-methoxynicotinate (400 mg, 1.36 mmol), 2-(pent-4-ynyl)isoindoline-1,3-dione (318 mg, 1.5 mmol), Pd(PPh3)2Cl2 (47 mg, 0.068 mmol), CuI (7.7 mg, 0.04 mmol) and triethylamine (400 uL) is stirred at room temperature for 20 hours. The mixture is diluted with water, made alkaline with K2CO3 and extracted with CHCl3. The organic layer is washed with brine, water and concentrated under vacuum. The title compound is purified by silica gel column chromatography using hexane/ethyl acetate as eluent. MS m/z 379.1 (M+1).

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer is washed with brine, water
  3. concentrationconcentrated under vacuum
  4. customThe title compound is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ca751bf952f41f6b8974fadc0585be5
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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