MAGNESIUM SILICATE (synthetic) → 3-(4-Benzyloxy-5-methoxy-2-triisopropylsilanylsulfanyl-phenyl)-5-methyl-[1,2,4]oxadiazole

HRID 2075965Notes

Reaction equation

HRID 2075965 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:11](I)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([Si:27]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[SH:28])([CH3:26])[CH3:25].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O-][Si]([O-])=O.[Mg+2]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:11]([S:28][Si:27]([CH:29]([CH3:31])[CH3:30])([CH:32]([CH3:34])[CH3:33])[CH:24]([CH3:25])[CH3:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 2724254Sodium bis(trimethylsilyl)amideHCID 3435097Tris(propan-2-yl)silanethiolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 508988613-(4-Benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxa-diazole

Product 1

HCID 670964453-(4-Benzyloxy-5-methoxy-2-triisopropylsilanylsulfanyl-phenyl)-5-methyl-[1,2,4]oxadiazole

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxadiazole (reference example 4-1) (0.7 g), triisopropylsilanethiol (0.391 mL), tris(dibenzylidene-acetone)dipalladium (0) (152 mg), (oxydi-2,1-phenylene)bis-(diphenylphosphine) (90 mg), sodium bis(trimethylsilyl)amide (1.0 mol/L tetrahydrofuran solution, 0.39 mL) and toluene (20 mL) was stirred at 80° C. for 2 hours under an argon atmosphere. After cooling to room temperature, Florisil (registered mark) (1 g) was added to the mixture. After stirring for 10 minutes, the mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure to give 3-(4-benzyloxy-5-methoxy-2-triisopropylsilanylsulfanyl-phenyl)-5-methyl-[1,2,4]oxadiazole.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringAfter stirring for 10 minutes
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-851bffeee6d046768f46b363f4c50a82
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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