Hydrochloric Acid → HCID 86593497, compound

HRID 2243161Notes

Reaction equation

HRID 2243161 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:6][CH:5]=1.[C:32](Cl)(=[O:36])[C:33](Cl)=[O:34].C([O-])(O)=[O:39].[Na+].Cl.[CH2:44]1COC[CH2:45]1>>[CH2:44]([O:34][C:33](=[O:39])[C:32]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:21][CH:20]=3)[CH:14]=2)[N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:31])=[CH:5][CH:6]=2)[CH:11]=1)=[O:36])[CH3:45]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 86593496HCID 86593496, compound

Product 1

HCID 86593497HCID 86593497, compound

Procedure

To a solution of 0.505 g (1.15 mmol) 1,5-bis-(4-trifluoromethoxy-phenyl)-1H-indole in 3 mL anhydrous THF was added 0.13 mL (2.9 mmol) oxalyl chloride. The solution was mixed at room temperature for 18 hr, upon which time the contents of the reaction vessel were drained into a vial containing 10 mL aqueous NaHCO3. The vial was capped and shaken and then the solution was acidified by the dropwise addition of 10 mL 2N aqueous HCl. The organic phase was removed and concentrated. The crude product was purified by RP-HPLC (See Note 1) to afford 0.142 g [1,5-bis-(4-trifluoromethoxy-phenyl)-1H-indol-3-yl]-oxo-acetic acid ethyl ester.

Workup

  1. additionThe solution was mixed at room temperature for 18 hr, upon which time the contents of the reaction vessel
  2. customThe vial was capped
  3. customThe organic phase was removed
  4. concentrationconcentrated
  5. customThe crude product was purified by RP-HPLC (See Note 1)

Sources & evidence

ORD record
ord-510e3605f9484ca080b98e284ce4f85b
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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