Water → diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate

HRID 1748292Notes

Reaction equation

HRID 1748292 reaction equation
[F:1][C:2]([F:35])([CH2:23]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)[CH:6]=[C:5]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[N-:36]=[N+:37]=[N-:38].[Na+].O>CN(C=O)C>[N:36]([CH2:23][C:2]([F:35])([F:1])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)[CH:6]=[C:5]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:37]=[N-:38]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86682393diethyl 1-(2,2-difluoro-3-{[(4-methylphenyl)sulfonyl]oxy}propyl)-1H-indole-2,6-dicarboxylate

Product 1

HCID 86682394diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylateYield 119.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of diethyl 1-(2,2-difluoro-3-{[(4-methylphenyl)sulfonyl]oxy}propyl)-1H-indole-2,6-dicarboxylate (4.7 g, 59% pure, 5.5 mmol) in DMF (40 mL) is added sodium azide (908 mg, 13.8 mmol). The mixture is heated at 95° C. for 40 h. Water (250 mL) is added and the mixture is extracted with EtOAc (3×250 mL). The organic layers are combined, washed with water (3×250 mL), dried (Na2SO4) and concentrated to afford the title crude compound (2.5 g) which is used in the next step without purification.

Workup

  1. extractionthe mixture is extracted with EtOAc (3×250 mL)
  2. washwashed with water (3×250 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7320d0e0dd343e9ad7f71585f952534
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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