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Hydrochloric Acid → HCID 21998712, compound

HRID 1976791
Notes
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Reaction equation

HRID 1976791 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=O)[C:19]([F:22])([F:21])[F:20])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]([F:22])([F:20])[F:21])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 219987215-Benzyloxy-1-trifluoroacetylindole

Product 1

HCID 21998712HCID 21998712, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 78A (1.98 g, 6.20 mmol) in THF (20 mL) at 0° C. was treated dropwise with 1M BH3 THF in THF (11.2 mL, 11.2 mmol), heated at reflux for 16 hours, cooled to 0° C., treated 6M HCl (approximately 1 mL), diluted with ethyl acetate (60 mL), washed with 10% NaHCO3 (30 mL) and brine (30 mL), dried (MgSO4), filtered, and concentrated to provide 1.56 g of the desired compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. washwashed with 10% NaHCO3 (30 mL) and brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38a39d16ff6b4f619f3c681cd44eeb08
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06228868B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes