Methanol → HCID 87545978, compound

HRID 1159819Notes

Reaction equation

HRID 1159819 reaction equation
CN([CH:4]=[O:5])C.[N:6]1([CH2:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH2:9][CH2:8][CH2:7]1.[H-].[Na+].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=1.C[OH:38]>Cl>[F:34][C:33]([F:36])([F:35])[C:4]([OH:5])=[O:38].[N:6]1([CH2:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[S:29]([C:26]2[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][C:25]=2[C:33]([F:36])([F:34])[F:35])(=[O:31])=[O:30])[CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27786084-Bromo-2-(trifluoromethyl)benzenesulfonyl chlorideHCID 68717531HCID 68717531, compound2×

Product 1

HCID 87545978HCID 87545978, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

DMF (1 ml) was added to a vial containing 4-(Azetidin-1-ylmethyl)-1H-indole (10 mg, 0.054 mmol; Intermediate 77) and 60% NaH (5.4 mg, 0.13 mmol) at rt. The mixture was stirred for 20 minutes before 4-bromo-2-(trifluoromethyl)benzenesulphonyl chloride (24.2 mg, 0.11 mmol) was added. The mixture was allowed to stir for 1 hour and 2 drops of 1N HCl was added. The mixture was diluted with MeOH, filtered and purified using preparative HPLC with ACE C8 5 μm (21.2×100 mm) column. Water containing 0.1% TFA and acetonitrile were used as mobile phases at a flow rate of 20 ml/min with gradient times of 11.5 min. Yield: 11 mg (35%). Light brown liquid. MS (ESI+) for C19H16BrF3N2O2S m/z 475 (M+H)+.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. custompurified
  4. customwere used as mobile phases at a flow rate of 20 ml/min with gradient times of 11.5 min

Sources & evidence

ORD record
ord-446008ef2bd84defbefdecb3a2ca2b61
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…