Tetrahydrofuran → HCID 67001330, compound

HRID 1434677Notes

Reaction equation

HRID 1434677 reaction equation
[H-].[Na+].[CH:3]([Si:6]([SH:13])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])([CH3:5])[CH3:4].Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]([CH2:26][O:27][CH3:28])[C:24]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)=[N:23][N:22]=2)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1[CH2:60][O:59][CH2:58]C1>C1C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][C:24]1[N:25]([CH2:26][O:27][CH3:28])[C:21]([C:18]2[CH:17]=[CH:16][C:15]([S:13][Si:6]([CH:7]([CH3:9])[CH3:8])([CH:10]([CH3:12])[CH3:11])[CH:3]([CH3:5])[CH3:4])=[CH:20][CH:19]=2)=[N:22][N:23]=1.[Cl:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][C:24]1[N:25]=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([S:13][Si:6]([CH:7]([CH3:9])[CH3:8])([CH:10]([CH3:12])[CH3:11])[CH:3]([CH3:5])[CH3:4])=[CH:20][CH:19]=2)[N:22]([CH2:58][O:59][CH3:60])[N:23]=1

Participants

9

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 67001368HCID 67001368, compound

Product 2

HCID 67001330HCID 67001330, compoundHCID 67001379HCID 67001379, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of NaH (1.5 mmol in 60% mineral oil) in THF (6 mL) at 0° C. was added triisopropylsilyl thiol (1.5 mmol) and the solution was stirred for 1 h before 3-(4-bromo-phenyl)-5-(3-chloro-benzyl)-4-methoxymethyl-4H-[1,2,4]triazole (1.5 mmol) in benzene (6 mL), triphenyl phosphine (0.6 mmol), and Pd2(dba)3 (0.08 mmol) were added. After bubbled argon through the solution for 15 min, the mixture was stirred at 80° C. for 18 h before it was cooled to room temperature. The reaction mixture was diluted with water (30 mL) and the resulting mixture was extracted with a solution of toluene and ethyl acetate (4:1) and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 3-(3-chloro-benzyl)-4-methoxymethyl-5-(4-triisopropylsilanylsulfanyl-phenyl)-4H-[1,2,4]triazole and 3-(3-chloro-benzyl)-1-methoxymethyl-5-(4-triisopropylsilanylsulfanyl-phenyl)-1H-[1,2,4]triazole (1.0 mmol) as a mixture of two isomers (4:1).

Workup

  1. additionwere added
  2. customAfter bubbled argon through the solution for 15 min
  3. temperaturewas cooled to room temperature
  4. additionThe reaction mixture was diluted with water (30 mL)
  5. extractionthe resulting mixture was extracted with a solution of toluene and ethyl acetate (4:1)
  6. washthe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6d39ab2b25fa48eb88b4d14a4b23f328
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

Loading…