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

HRID 502132Notes

Reaction equation

HRID 502132 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) is heated at 125° C. for 2 h. The reaction mixture is cooled and partitioned in H2O and EtOAc. The organic phase is dried and concentrated and the product is purified by silica gel chromatography (EtOAc/CH2Cl2 5-10%). The product containing fractions are combined and concentrated and the solid is 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 is cooled
  2. custompartitioned in H2O
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customthe product is purified by silica gel chromatography (EtOAc/CH2Cl2 5-10%)
  6. additionThe product containing fractions
  7. concentrationconcentrated
  8. customthe solid is triturated with hexanes

Sources & evidence

ORD record
ord-7b452f31fbb64d39ba9b6f44cad0cfcc
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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