Sodium Hydroxide → HCID 9968883, compound

HRID 1582442Notes

Reaction equation

HRID 1582442 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])=[C:7]3[CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1.[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([C:22](=[O:27])[C:23]([F:25])([F:24])[F:26])=[C:7]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22720895HCID 22720895, compound

Product 1

HCID 9968883HCID 9968883, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-[8-bromo-11-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethanone (105 mg, 0.23 mmol) in methanol (3 mL) is treated with 1M sodium hydroxide (1 mL, 1 mmol). After 30 min, the reaction is diluted with water (15 mL) and extracted twice with dichloromethane (20 mL). The combined organics are washed with brine (15 mL), dried over MgSO4, filtered, and concentrated to give a crude solid. This material is recrystallized from ethyl acetate/heptane to afford 48 mg of a white solid. IR (drift) 1666, 1508, 1464, 1426, 1282, 1248, 1211, 1201, 1181, 1130, 1060, 1043, 956, 939, 757 cm−1.

Workup

  1. extractionextracted twice with dichloromethane (20 mL)
  2. washThe combined organics are washed with brine (15 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid
  7. customThis material is recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-79168be1fc0944588a2b05813c655edc
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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