Triethylamine → HCID 58975081, compound

HRID 737066Notes

Reaction equation

HRID 737066 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:16][C:17]1[CH:36]=[CH:35][C:20]([CH2:21][NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[O:24])=[CH:19][CH:18]=1.CCN(CC)CC.CC(N(C)C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][NH:22][C:23](=[O:24])[C:25]2[CH:30]=[CH:29][C:28]([S:31]([N:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:8]3)(=[O:32])=[O:33])=[CH:27][CH:26]=2)=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 516892Sodium BicarbonateHCID 109323533-phenyl-2,3-dihydro-1H-indoleHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 58975081HCID 58975081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir 3-phenyl-2,3-dihydro-1H indole (0.233 g, 1.19 mmol), 4-(4-fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (1 equiv.), Et3N (0.50 mL, 0.36 g, 3.57 mmol), DMA (0.015 g, 0.123 mmol) in CH2Cl2 (45 mL) overnight under N2. Dilute the CH2Cl2 to 150 mL and pour into a saturated solution of NaHCO3 (50 mL) and stir for 15 minutes. Separate the organic layer and wash with H2O (100 mL), extract with 1N HCl (2×75 mL), wash with brine, separate and dry (MgSO4). Filter and evaporate followed by chromatography on the ISCO using a 40 g silica gel column and elute with EtOAc-hexane 90-100%) to give 0.33 g of the racemic compound.

Workup

  1. customSeparate the organic layer
  2. washwash with H2O (100 mL)
  3. extractionextract with 1N HCl (2×75 mL)
  4. washwash with brine
  5. customseparate
  6. dry with materialdry (MgSO4)
  7. filtrationFilter
  8. customevaporate
  9. washelute with EtOAc-hexane 90-100%)

Sources & evidence

ORD record
ord-ef42f56319d34c92ad814459e7665666
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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