Hydrochloric Acid → HCID 44179973, compound

HRID 1911236Notes

Reaction equation

HRID 1911236 reaction equation
C[Al](C)C.[NH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)[C:21]([C:34](OCC)=[O:35])=[CH:20]2.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:6]([NH:5][C:34]([C:21]2[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:23]3[C:19]([CH:20]=2)=[CH:18][C:17]([F:16])=[CH:25][CH:24]=3)=[O:35])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 113753-AminoquinolineHCID 16682925TrimethylaluminumHCID 57431514Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate

Product 1

HCID 44179973HCID 44179973, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

1.19 mL (2.38 mmol) of a 2M solution of trimethylaluminium in toluene are added dropwise to a solution, stirred at 0° C. under an inert atmosphere, of 0.274 g (1.9 mmol) of 3-aminoquinoline in 40 mL of dry toluene. The mixture is then stirred at 50° C. After 15 minutes, a solution of 0.5 g (1.59 mmol) of ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate (WO2006/024776) in 10 mL of toluene is added dropwise. 15 mL of 1N hydrochloric acid solution and 100 mL of ethyl acetate are added to the mixture. The organic phase is separated out and then washed successively with 20 mL of 1N hydrochloric acid solution, 20 mL of water and 20 mL of saturated sodium chloride solution, and then concentrated under reduced pressure. The product thus obtained is triturated in 10 mL of hot toluene. A precipitate is collected by filtration. After drying, 295 mg of the expected product are thus isolated.

Workup

  1. customThe organic phase is separated out
  2. washwashed successively with 20 mL of 1N hydrochloric acid solution, 20 mL of water and 20 mL of saturated sodium chloride solution
  3. concentrationconcentrated under reduced pressure
  4. customThe product thus obtained
  5. customis triturated in 10 mL of hot toluene
  6. filtrationA precipitate is collected by filtration
  7. customAfter drying

Sources & evidence

ORD record
ord-7f1770abc909484387a848f28b29cc9d
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

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