Chlorosuccinimide → 3-Chloro-5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indole

HRID 423297Notes

Reaction equation

HRID 423297 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[NH:26][CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Cl:37])C(=O)C1>C(Cl)Cl>[Cl:37][C:24]1[C:23]2[C:27](=[CH:28][CH:29]=[C:21]([C:18]3[N:17]=[C:16]([C:9]4[S:10][C:11]([C:12]([F:15])([F:14])[F:13])=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=4)[O:20][N:19]=3)[CH:22]=2)[NH:26][CH:25]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

Product 1

HCID 593183433-Chloro-5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indoleYield 16.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

D2 (200 mg) and NCS (65 mg) were dissolved in DCM (5 ml) and stirred overnight at room temperature. The reaction mixture was then partitioned between DCM and H2O. The DCM solution was evaporated to dryness and purified on a Biotage silica cartridge, eluting with a 25-75% mixture of diethyl ether in hexane. This gave the title compound (36 mg) as a brown solid. A second batch of the title compound was also obtained from this purification (86 mg) as a brown solid. δH (CDCl3, 400 MHz): 7.28 (1H, m), 7.45-7.54 (6H, m), 7.93 (1H, s), 8.05 (1H, d), 8.28 (1H, br s), 8.49 (1H, s). MS (ES): C21H11ClF3N3OS requires 445; found 444 (M−H+).

Workup

  1. customThe reaction mixture was then partitioned between DCM and H2O
  2. customThe DCM solution was evaporated to dryness
  3. custompurified on a Biotage silica cartridge
  4. washeluting with a 25-75% mixture of diethyl ether in hexane

Sources & evidence

ORD record
ord-41150b8ae4ab410f884a2e746a5d460b
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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