Ethanol → HCID 59146119, compound

HRID 1512856Notes

Reaction equation

HRID 1512856 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][C:6]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5]2.S(Cl)(Cl)=O.[CH2:21](O)[CH3:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][C:6]([CH2:12][CH2:13][C:14]([O:16][CH2:21][CH3:22])=[O:15])=[CH:5]2

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 591460895-Bromo-7-fluoro-1H-indole-2-propanoic acid

Product 1

HCID 59146119HCID 59146119, compound

Procedure

To a suspension of 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoic acid (D160) (1 g) in ethanol (15 mL) was added thionyl dichloride (0.083 g). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was diluted with EtOAc (30 mL). The organic phase was washed with 2 M sodium carbonate solution (25 mL) and water (50 mL), dried over sodium sulphate and evaporated in vacuo to give the crude product ethyl 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoate (D161) (1.1 g) as a yellow solid. δH (CDCl3, 400 MHz): 1.23 (3H, t), 2.73 (2H, t), 3.06 (2H, t), 4.16 (2H, m), 6.20 (1H, s), 7.05 (1H, d), 7.41 (1H, s), 8.85 (1H, s).

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was diluted with EtOAc (30 mL)
  3. washThe organic phase was washed with 2 M sodium carbonate solution (25 mL) and water (50 mL)
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0fb04b0d2614260990eff83c5feae1a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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