Triethylamine → HCID 58399152, compound

HRID 475481Notes

Reaction equation

HRID 475481 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][N:5]12.[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:14][CH:11]2[CH2:10][N:5]3[C:6]4[C:2]([CH:3]=[C:4]3[CH2:13][CH2:12]2)=[CH:1][CH:9]=[CH:8][CH:7]=4)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 19696439HCID 19696439, compound

Product 1

HCID 58399152HCID 58399152, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (+/−) 6,7,8,9-tetrahydropyrido[1,2-α]indol-7-amine from Step 9 in CH2Cl2 (0.14 M) at rt were added 4-fluorobenzenesulfonyl chloride (1.2 equiv.), triethylamine (5 equiv.) and DMAP (0.03 equiv). The reaction mixture was stirred at rt for 2 h. It was poured into aqueous NaHCO3 and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried with MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel using using a CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hex (0:100 to 50:50 for 15 min, then at 50:50 for 5 min) to give the title compound (78%) as a light yellow foam.

Workup

  1. extractionextracted with dichloromethane (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel using
  6. washeluting with EtOAc/Hex (0:100 to 50:50 for 15 min

Sources & evidence

ORD record
ord-2c821575b16d4e95b4e0197ba214ed3a
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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