Toluene → HCID 58188178, compound

HRID 1845335Notes

Reaction equation

HRID 1845335 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]([OH:19])[CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([Sn](CCCC)(CCCC)CCCC)=[N:25][CH:26]=1.C1(C)C=CC=CC=1>[Cl-].[Na+].O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:15]([N:14]([CH2:17][CH3:18])[CH2:13][CH:12]([C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:24]2[CH:23]=[CH:22][C:21]([CH3:20])=[CH:26][N:25]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[OH:19])[CH3:16]

Participants

6

Reactant 3

HCID 1140TolueneHCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 58187991HCID 58187991, compound

Product 1

HCID 58188178HCID 58188178, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of methyl 3-bromo-5-(2-(diethylamino)-1-hydroxyethyl)benzoate (80 mg, 0.24 mmol), 5-methyl-2-(tributylstannyl)pyridine (100 μL, 0.30 mmol), tetrakis(triphenylphosphine)-palladium(0) (14 mg, 0.012 mmol) and toluene (2.6 mL) under argon was subjected to microwave irradiation at 120° C. for 2 hours. The mixture was cooled to room temperature, poured into brine (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (0-100% EtOAc/hexane) to yield the title compound as a yellow oil. LC-MS: 343.7 [M+1]+.

Workup

  1. customirradiation at 120° C. for 2 hours
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-02dcc897891a46d29126a5ee9db8d158
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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