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

HRID 2199744Notes

Reaction equation

HRID 2199744 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-c74e5a0c8f744890a08816e45f0c8522
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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