Hydrochloric Acid → {1-[4-(Cyclohexyl-methyl-sulfamoyl)-benzyl]-5-fluoro-2-methyl-1H-indol-3-yl}-acetic acid

HRID 1364587Notes

Reaction equation

HRID 1364587 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]=1[CH3:16])C.[H-].[Na+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH3:32])(=[O:30])=[O:29])=[CH:24][CH:23]=1.Cl>CS(C)=O.O>[CH:33]1([N:31]([CH3:32])[S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][N:8]3[C:9]4[C:14](=[CH:13][C:12]([F:15])=[CH:11][CH:10]=4)[C:6]([CH2:5][C:4]([OH:3])=[O:17])=[C:7]3[CH3:16])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 11665843Ethyl (5-fluoro-2-methyl-1H-indol-3-yl)acetateHCID 190232724-(bromomethyl)-N-cyclohexyl-N-methylbenzenesulfonamide

Product 1

HCID 66936919{1-[4-(Cyclohexyl-methyl-sulfamoyl)-benzyl]-5-fluoro-2-methyl-1H-indol-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirring suspension of (5-fluoro-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester (100 mg, 0.43 mmol) in dry DMSO (1 ml), is added NaH (29 mg, 0.73 mmol). The reaction mixture is stirred at room temperature for 15 min after which time 4-bromomethyl-N-cyclohexyl-N-methyl-benzenesulfonamide (149 mg, 0.43 mmol) is added. Reaction mixture is diluted with water (10 ml) and treated with 1N HCl aq to acidic pH. The product is extracted in 1:1 EtOAc:Et2O (20 ml), washed with brine, dried (MgSO4) and evaporated in vacuo. The crude reaction mixture is purified by preparative MS-directed HPLC to afford the title compound; [M+H]+ 474.

Workup

  1. additionis added
  2. customReaction mixture
  3. extractionThe product is extracted in 1:1 EtOAc
  4. washEt2O (20 ml), washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe crude reaction mixture
  8. customis purified by preparative MS-directed HPLC

Sources & evidence

ORD record
ord-82bee586e0764ae5b51f84bb79c4f347
Source dataset
uspto-grants-2011_02
Patent number
US07888383B2

Reaction notes

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