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

HRID 423296Notes

Reaction equation

HRID 423296 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C1C(=O)N([Cl:33])C(=O)C1>C(Cl)Cl>[Cl:33][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([C:14]3[N:13]=[C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[CH:3]=4)[O:16][N:15]=3)[CH:18]=2)[NH:22][CH:21]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 593183535-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

Product 1

HCID 593183613-Chloro-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indoleYield 12.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

D5 (300 mg) and NCS (113 mg) were dissolved in DCM (4.2 ml) and stirred overnight at room temperature. The reaction mixture was then diluted with DCM and washed with H2O. The aqueous solution was extracted with two further portions of DCM and the combined organic solutions were evaporated to dryness. The crude product was triturated with methanol to give the title compound (42 mg) as a brown solid. The methanol was then evaporated and the resultant brown solid triturated with DCM to give a second batch of the title compound (205 mg) as a brown solid. δH (d6-DMSO, 400 MHz): 1.37 (6H, d), 4.89 (1H, septet), 7.45 (1H, d), 7.62 (1H, d), 7.70 (1H, s), 7.93 (1H, d), 8.15 (1H, d), 8.24 (1H, s), 8.25 (1H, s), 11.77 (1H, s). MS (ES): C19H1535Cl2N3O2 requires 387; found 388 (MH+).

Workup

  1. washwashed with H2O
  2. extractionThe aqueous solution was extracted with two further portions of DCM
  3. customthe combined organic solutions were evaporated to dryness
  4. customThe crude product was triturated with methanol

Sources & evidence

ORD record
ord-92ca3f489b7b4e9d8109c6984cb2658d
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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