2-Bromo-1,1-dimethoxyethane → HCID 59426268, compound

HRID 252511Notes

Reaction equation

HRID 252511 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=[S:16])[NH2:15])=[CH:4]1)[CH3:2].CO[CH:19](OC)[CH2:20]Br>C(COC)OC>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]2[S:16][CH:19]=[CH:20][N:15]=2)=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethane3×HCID 59426224HCID 59426224, compound

Product 1

HCID 59426268HCID 59426268, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

1-Ethyl-6-methoxy-1H-indole-3-thiocarboxamide (83 mg, 0.36 mmol), glyme (3.6 mL) and bromoacetaldehyde dimethyl acetal (220 μL, 1.86 mmol) are heated at 80° C. for 16 h. More bromoacetaldehyde dimethyl acetal (250 μL) is added. This is heated at 80° C. for 2 h. Addition of 250 μL more bromoacetaldehyde dimethyl acetal is followed by heating for another 2 hours. The reaction mixture is cooled to room temperature, absorbed onto silica and purified by silica gel chromatography (hexanes/EtOAc, 7/3) to afford 1-ethyl-6-methoxy-3-thiazol-2-yl-1H-indole as a brown oil (44 mg, 47%).

Workup

  1. temperatureby heating for another 2 hours
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customabsorbed onto silica
  4. custompurified by silica gel chromatography (hexanes/EtOAc, 7/3)

Sources & evidence

ORD record
ord-f746402c42754cd98b9426108e72ca8d
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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