Diethyl Ether → HCID 68006769, compound

HRID 2401773Notes

Reaction equation

HRID 2401773 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]([C:14]3[N:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=3)=[C:10]([CH:12]=[O:13])[N:11]=2)=[CH:3][CH:2]=1.O1[CH2:31][CH2:30][CH2:29][CH2:28]1.CCO[CH2:35][CH3:36].[NH4+].[Cl-:38]>ClC1C=CC([Mg]Br)=CC=1.CCOC(C)=O>[Cl:38][C:28]1[CH:36]=[CH:35][C:31]([CH:12]([C:10]2[N:11]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[S:8][C:9]=2[C:14]2[N:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=2)[OH:13])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86667469HCID 86667469, compound

Product 1

HCID 68006769HCID 68006769, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 178478191HCID 178478191, compoundSolvent

Procedure

To a solution of 2-pyridin-4-yl-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazole-4-carbaldehyde (280.0 mg, 0.722 mmol) in tetrahydrofuran (4.0 mL, 40 mmol), 1 M 4-chlorophenyl magnesium bromide in ether (4.0 mL, 4 mmol) was added and the mixture was stirred for 40 min at rt. After the reaction was completed a 5% aqueous solution of NH4Cl (10 mL) and EtOAc (10 mL) were added and the resulting bi-phasic mixture was vigorously stirred for 15 min then the aqueous phase was discarded. The organic phase was washed with brine (5 mL) then dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (SiO2, elution with 20-80% EtOAc in hexane) to give the title compound as a white solid (230 mg, 73.6%). LCMS: (FA) ES+ , 500. 1H NMR (400 MHz, d6-DMSO) δ: 8.96 (s, 1H), δ 8.70-8.72 (dd, J=1.75 Hz, 2H), 7.87-7.89 (dd, J=1.75, 2H), 7.32-7.37 (m, 2H), 7.55-7.58 (m, 3H), 6.85-6.87 (d, J=5.5 Hz, 1H), 6.15-6.17 (d, J=5.5 Hz, 1H), 5.6 (s, br, 2H), 3.65-3.67 (m, 2H), 0.850-0.90 (m, 2H), −0.05 (s, 9H).

Workup

  1. additionwere added
  2. stirringthe resulting bi-phasic mixture was vigorously stirred for 15 min
  3. washThe organic phase was washed with brine (5 mL)
  4. dry with materialthen dried over anhydrous MgSO4
  5. customInsoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (SiO2, elution with 20-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-63de6ffe92a4422db2c5e1e8b8fc3cf7
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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