5-Methyl-2-(tri-n-butylstannyl)pyridine → Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

HRID 2278719Notes

Reaction equation

HRID 2278719 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](I)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([Sn](CCCC)(CCCC)CCCC)=[N:18][CH:19]=1>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.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:17]2[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][N:18]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 21942573Methyl 3-bromo-5-iodobenzoate

Product 1

HCID 59599704Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A microwave vial was charged with methyl 3-bromo-5-iodobenzoate (2.00 g, 5.87 mmol), 5-methyl-2-(tributylstannyl)pyridine (2.24 g, 5.87 mmol), tetrakis(triphenylphosphine)palladium(0) (339 mg, 0.29 mmol) and 1,4-dioxane (30 mL). The reaction mixture was subjected to microwave irradiation at 120° C. for 1 hour. The reaction was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography to afford the product as a white solid. 1H NMR (400 Hz, DMSO-d6): 8.64 (t, J=1.51 Hz, 1H), 8.55 (m, 1H), 8.52 (t, J=1.89 Hz, 1H), 8.07 (t, J=1.89 Hz, 1H), 8.03 (d, J=8.31 Hz, 1H), 7.75 (dd, J=8.31 & 2.27 Hz, 1H), 3.91 (s, 1H), 2.36 (s, 1H).

Workup

  1. customirradiation at 120° C. for 1 hour
  2. filtrationThe reaction was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4af04d1c89ff4bbbbebaea416d776c70
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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