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Hydrochloric Acid → {5-Fluoro-2-methyl-1-[4-(morpholine-4-sulfonyl)-benzyl]-1H-indol-3-yl}-acetic acid

HRID 1364586
Notes
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Reaction equation

HRID 1364586 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]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1.Cl>CS(C)=O.O>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:7]([CH3:16])=[C:6]2[CH2:5][C:4]([OH:3])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27796804-((4-(Bromomethyl)phenyl)sulfonyl)morpholineHCID 11665843Ethyl (5-fluoro-2-methyl-1H-indol-3-yl)acetate

Product 1

HCID 23627406{5-Fluoro-2-methyl-1-[4-(morpholine-4-sulfonyl)-benzyl]-1H-indol-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 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-(4-bromomethyl-benzenesulfonyl)-morpholine (136 mg, 0.43 mmol) is added. The reaction mixture is diluted with water (2 ml) and treated with 1N HCl aq to acidic pH. The crude reaction mixture is purified by reverse phase chromatography on a C18 Isolute™ cartridge (70 g) eluting in 0-100% MeCN in water using a FlashMaster Personal™ and GradMaster™; [M+H]+ 448.

Workup

  1. additionis added
  2. customThe crude reaction mixture
  3. customis purified by reverse phase chromatography on a C18 Isolute™ cartridge (70 g)
  4. washeluting in 0-100% MeCN in water using a FlashMaster Personal™ and GradMaster™

Sources & evidence

ORD record
ord-27fcca35f09f47ed82928cc99ad5980f
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888383B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes