Hydrochloric Acid → 3-(7-Bromo-2-(ethoxycarbonyl)-4-fluoro-1h-indol-3-yl)propanoic acid

HRID 2095271Notes

Reaction equation

HRID 2095271 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:23])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][C:18]([O:20]CC)=[O:19].Cl>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:23])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68937923ethyl 7-bromo-3-(3-ethoxy-3-oxopropyl)-4-fluoro-1H-indole-2-carboxylate

Product 1

HCID 689411293-(7-Bromo-2-(ethoxycarbonyl)-4-fluoro-1h-indol-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of EXAMPLE 402A (2.3 g) in acetic acid (40 ml) was added concentrated hydrochloric acid (3 ml). The mixture was heated at 80° C. for 4 hours. After cooling to room temperature, precipitation of the product occurred. Water (50 mL) was added to further induce precipitation. The solid was filtered, rinsed with water and dried in vacuo.

Workup

  1. temperatureAfter cooling to room temperature
  2. customprecipitation of the product
  3. additionWater (50 mL) was added to further induce precipitation
  4. filtrationThe solid was filtered
  5. washrinsed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-827faf952f194356ad7a40e02ac86e90
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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