1,2-Dimethoxyethane → Ethyl 5-chloro-2-(quinolin-6-yl)benzoate

HRID 2042102Notes

Reaction equation

HRID 2042102 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N:14]1[C:23]2[C:18](=[CH:19][C:20](B(O)O)=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(COC)OC>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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:14]=[CH:15][CH:16]=[CH:17]3)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 4192671Quinolin-6-ylboronic Acid (contains varying amounts of Anhydride)HCID 51341862Ethyl 5-chloro-2-iodobenzoate

Product 1

HCID 67253873Ethyl 5-chloro-2-(quinolin-6-yl)benzoateYield 39.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A degassed mixture of ethyl 5-chloro-2-iodobenzoate (0.621 g, 2.00 mmol), Pd(PPh3)4 (0.116 mg, 0.1 mmol), quinolin-6-ylboronic acid (0.381 g, 2.2 mmol), K2CO3 (0.553 g, 4.0 mmol), dimethoxyethane (20 mL), and water (5 mL) was heated under reflux overnight. Solvents were removed under reduced pressure. The residue was diluted with sat'd NH4Cl (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried (MgSO4), concentrated in vacuo and purified by chromatography to afford ethyl 5-chloro-2-(quinolin-6-yl)benzoate (0.244 g, 39% yield) as a colorless oil. MS (ESI) m/z: 312.0 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customSolvents were removed under reduced pressure
  4. additionThe residue was diluted with sat'd NH4Cl (15 mL)
  5. extractionextracted with EtOAc (3×30 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-b5ecbd688b034e24845d8fdbe1d4dd0c
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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