Sodium Iodide → HCID 178466555, compound

HRID 1433221Notes

Reaction equation

HRID 1433221 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:26]=[CH:25][C:18]2[NH:19][C:20]([CH:22](Cl)[CH3:23])=[N:21][C:17]=2[CH:16]=1)(=[O:8])=[O:7])(C)(C)C.[F:27][C:28]([F:37])([F:36])[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-]>CN(C=O)C.ClCCCl.C(O)(C(F)(F)F)=O>[F:27][C:28]([F:36])([F:37])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:22]([C:20]2[NH:19][C:18]3[CH:25]=[CH:26][C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[S:6]([NH2:5])(=[O:7])=[O:8])=[CH:16][C:17]=3[N:21]=2)[CH3:23])=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 178456119HCID 178456119, compound

Product 1

HCID 178466555HCID 178466555, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-tert-butyl-2-[2-(1-chloro-ethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide (0.042 g, 0.107 mmol), 4-trifluoromethyl-phenol (0.069 g, 0.428 mmol), Na2CO3 (0.045 g, 0.428 mmol), and NaI (0.064 g, 0.428 mmol) in DMF at rt (2 mL) was stirred for 24 hours. The reaction mixture was purified by chromatography (silica, hexanes: EtOAc, 1:1) to afford the protected product. This material dissolved in 1,2-dichloroethane (1 mL) and TFA (1 mL), was heated to 60° C. for 2 hours, and then cooled. The solvent was evaporated and the resulting crude material was purified by chromatography (silica, EtOAc: hexanes, 2:1) afforded the title compound as a pale yellow oil (0.033, 67%). 1H NMR (400 MHz, CD3OD) δ (ppm): 8.14 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 7.70 (dd, 1H, J=1.6 Hz, J=0.8 Hz), 7.67-7.58 (m, 4H), 7.55 (td, 1H, J=8.6 Hz, J=1.6 Hz), 7.39 (td, 2H, J=9.0 Hz, J=1.6 Hz), 7.20 (d, 2H, J=8.8 Hz), 5.91 (q, 1H), 1.87 (d, 3H, J=6.8 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C24H22F3N4O3S: 503.5 (M+MeCN+H), Found 503.2.

Workup

  1. customThe reaction mixture was purified by chromatography (silica, hexanes: EtOAc, 1:1)
  2. customto afford the protected product
  3. temperaturecooled
  4. customThe solvent was evaporated
  5. customthe resulting crude material was purified by chromatography (silica, EtOAc: hexanes, 2:1)

Sources & evidence

ORD record
ord-c7d79ca522374c7ba9c9e2b3df627a6c
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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