Trifluoroacetic acid → 3-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1H-indazole

HRID 1047530Notes

Reaction equation

HRID 1047530 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:27]=3)[CH:24]=2)[N:19](C2CCCCO2)[N:18]=1>C(Cl)Cl>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:27]=3)[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1363522463-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 1362325493-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1H-indazoleYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL, 6.490 mmol) was added to a solution 3-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (7 mg, 0.015 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (4 mg) as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 8.84 (s, 1H), 8.39 (m, 1H), 7.17 (m, 1H), 7.95 (m, 1H), 7.85 (m, 2H), 7.78-7.73 (m, 3H), 7.28 (m, 2H); ESI-MS [M+H]+: 389.3.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by flash chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-7d42a9d9f36f4952a2f25416a29da9bc
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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