Triethylamine → HCID 67338415, compound

HRID 557196Notes

Reaction equation

HRID 557196 reaction equation
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][NH:18][CH2:19][CH2:20]O)[CH:10]=[CH:9]1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].[H-].[Na+]>O1CCCC1.CN(C)C=O>[CH3:22][S:23]([CH:13]1[CH2:14][C:15]2[CH:17]=[N:18][CH:19]=[CH:20][N:8]3[C:16]=2[C:11]([CH:10]=[CH:9]3)=[CH:12]1)(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 219500502-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

Product 1

HCID 67338415HCID 67338415, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add triethylamine (3.19 g, 31.56 mmol) to a solution of 2-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol (2.0 g, 10.52 mmol) in tetrahydrofuran (50 ml) at 0° C. Slowly add 1.75 mL (22.09 mMol) methanesulfonyl chloride and allow the reaction to warm to room temperature. Quench the reaction with saturated aqueous sodium bicarbonate and extract into ethyl acetate. Combine the organic layers, wash sequentially with saturated aqueous ammonium chloride, water, and saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure. Add sodium hydride (0.8416 g, 21.04 mmol, 60% dispersion in mineral oil) to the resulting oil in dimethylformamide (20 ml). Quench the reaction with saturated aqueous sodium bicarbonate, concentrate to about 10 ml and extract into ethyl acetate. Combine the organic layers, wash sequentially with saturated ammonium chloride, water, and saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure. Purification by flash chromatography, eluting with ethyl acetate:hexane gradient gives the title compound as an off-white solid.

Workup

  1. customthe reaction
  2. customQuench
  3. customthe reaction with saturated aqueous sodium bicarbonate
  4. extractionextract into ethyl acetate
  5. washwash sequentially with saturated aqueous ammonium chloride, water, and saturated aqueous sodium chloride
  6. dry with materialdry over magnesium sulfate
  7. concentrationconcentrate under reduced pressure
  8. customQuench
  9. customthe reaction with saturated aqueous sodium bicarbonate
  10. concentrationconcentrate to about 10 ml
  11. extractionextract into ethyl acetate
  12. washwash sequentially with saturated ammonium chloride, water, and saturated aqueous sodium chloride
  13. dry with materialdry over magnesium sulfate
  14. concentrationconcentrate under reduced pressure
  15. customPurification by flash chromatography
  16. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0a80a068b9684ab6ba8fef2b067fa9a5
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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