Triethylamine → 3-(1-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

HRID 2267490Notes

Reaction equation

HRID 2267490 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:32]=[C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](=[O:42])[N:34]1[CH2:43][CH2:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[O:42]=[C:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:33](=[O:32])[N:34]1[CH2:43][CH2:44][S:45]([N:22]1[CH2:23][CH2:24][CH:19]([C:10]2[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[NH:12][CH:11]=2)[CH2:20][CH2:21]1)(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 114271625-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 590033673-(1-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (84.8 mg, 0.265 mmol) in CH2Cl2 at 0° C., triethylamine (0.15 mL, 1.06 mmol) and 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonyl chloride (87.03 mg, 0.32 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was partitioned between CH2Cl2 and water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic phase washed with brine, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give the crude product (90 mg, 61%).

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. washThe combined organic phase washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-926cc8cdf5c446aab40b4d21f2d5d256
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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