Triphenylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]thio}-2-methylphenyl)oxy]acetate

HRID 1391799Notes

Reaction equation

HRID 1391799 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[CH:3]=1.[Br:16][C:17]1[N:22]=[C:21]([CH:23](O)[CH2:24][O:25][CH2:26][CH3:27])[CH:20]=[CH:19][CH:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[Br:16][C:17]1[N:22]=[C:21]([CH:23]([S:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[CH:3]=2)[CH2:24][O:25][CH2:26][CH3:27])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 586298281-(6-Bromo-2-pyridinyl)-2-(ethyloxy)ethanol

Product 1

HCID 58629945Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]thio}-2-methylphenyl)oxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (ethyl [(4-mercapto-2-methylphenyl)oxy]acetate) (386 mg, 1.71 mmol), 1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethanol (352 mg, 1.43 mmol) and PPh3 (450 mg, 1.72 mmol) in DCM (17 mL) at 0° C. under nitrogen was stirred for 10 mins and then treated drop-wise with DIAD (0.34 mL, 1.73 mmol). The resulting mixture was then stirred, with slow warming to ambient temperature over 18 h. The mixture was then reduced under vacuum and the resulting yellow oil purified by SPE (silica, 20 g cartridge), eluting with cyclohexane:EtOAc (gradient 15:1 to 5:1). Further purification using the OPTIX-SPE (C18 cartridge, 50 g) eluting with 60-80% MeCN (+0.05% HCOOH) in H2O (+0.01% HCOOH) over 56 mins afforded the title compound as an oil (232 mg).

Workup

  1. customthe resulting yellow oil purified by SPE (silica, 20 g cartridge)
  2. washeluting with cyclohexane
  3. customFurther purification
  4. washeluting with 60-80% MeCN (+0.05% HCOOH) in H2O (+0.01% HCOOH) over 56 mins

Sources & evidence

ORD record
ord-baea51d241ba4cbf8d526c58ea1d4d10
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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