2-Bromo-1,1-dimethoxyethane → HCID 11499995, compound

HRID 907114Notes

Reaction equation

HRID 907114 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:16]([NH2:18])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].CO[CH:21](OC)[CH2:22]Br>COCCOCCOC>[CH2:14]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=2)[C:9]([C:16]2[O:17][CH:21]=[CH:22][N:18]=2)=[CH:10]1)[CH3:15]

Participants

4

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 59426369HCID 59426369, compound

Product 1

HCID 11499995HCID 11499995, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 150 mg (0.61 mmol) of 6-methoxycarbonyl-1-ethyl-1H-indole-3-carboxamide in diglyme (3.6 mL), and bromoacetaldehyde dimethyl acetal (430 μL, 3.7 mmol) was heated at 125° C. for 2 h. The reaction mixture was cooled and partitioned in H2O and EtOAc. The organic phase was dried and concentrated and the product was purified by silica gel chromatography (EtOAc/CH2Cl2 5-10%). The product containing fractions were combined and concentrated and the solid was triturated with hexanes to yield methyl 1-ethyl-3-oxazol-2-yl-1H-indole-6-carboxylate (75 mg, 46%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned in H2O
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customthe product was purified by silica gel chromatography (EtOAc/CH2Cl2 5-10%)
  6. additionThe product containing fractions
  7. concentrationconcentrated
  8. customthe solid was triturated with hexanes

Sources & evidence

ORD record
ord-88a2982b67fa4aa6a9f6e5ac0604fc3f
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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