Pyridine → HCID 11702291, compound

HRID 2265771Notes

Reaction equation

HRID 2265771 reaction equation
[C:1]([Si:5]1([C:13]([CH3:16])([CH3:15])[CH3:14])[O:10][CH2:9][CH:8]([CH2:11]O)[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:24][CH2:11][CH:8]1[CH2:9][O:10][Si:5]([C:13]([CH3:16])([CH3:15])[CH3:14])([C:1]([CH3:4])([CH3:3])[CH3:2])[O:6][CH2:7]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11651695HCID 11651695, compound

Product 1

HCID 11702291HCID 11702291, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Compound 19n (123 mg, 0.5 mmol) was dissolved in dichloromethane (10 mL) and cooled to −10° C. with an ethanol-ice bath. Pyridine (1 mL) was added followed by carbon tetrabromide (220 mg, 0.66 mmol). Triphenylphosphine (174 mg, 0.66 mmol) was added in portions and the solution was stirred at −10° C. for 2 hr then raised to room temperature overnight. Solvent was removed under reduced pressure and residue was applied for silica gel column chromatography (10% ethyl acetate in hexane) to afford compound 20n (130 mg, 84%): 1H NMR δ 4.20 (m, 2H), 3.93 (t, 2H), 3.20 (d, 2H, J=6.19 Hz), 2.39 (m, 1H), 1.04 (s, 9H), 1.01 (s, 9H).

Workup

  1. temperaturethen raised to room temperature overnight
  2. customSolvent was removed under reduced pressure and residue

Sources & evidence

ORD record
ord-3b588f2ae3b944eaa1d47348bff76605
Source dataset
uspto-grants-2010_12
Patent number
US07858072B2

Reaction notes

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