Hydrochloric Acid → [3-(Biphenyl-4-ylsulfanyl)-5-fluoro-2-methyl-indol-1-yl]-acetic Acid

HRID 18495Notes

Reaction equation

HRID 18495 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[CH:5]2.[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.II.Cl>CN(C=O)C.O>[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:18][C:19]([S:22][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[CH3:15])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 27604144-Phenylbenzene-1-thiolHCID 674666192(5-fluoro-2-methyl-1H-indol-1-yl)acetic acid

Product 1

HCID 23624516[3-(Biphenyl-4-ylsulfanyl)-5-fluoro-2-methyl-indol-1-yl]-acetic AcidYield 0%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-fluoro-2-methyl-indol-1-yl)-acetic acid (0.5 g) and biphenyl-4-thiol (0.19 g) in DMF (5 ml) was added iodine (0.25 g). After stirring at RT overnight the mixture was poured into water, the pH adjusted to 3 using 1M HCl and the organics extracted with EtOAc. The EtOAc extractions were combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give crude material. Purification using RPHPLC gave the title compound as a pink solid (0.1 μg).

Workup

  1. extractionthe organics extracted with EtOAc
  2. extractionThe EtOAc extractions
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give crude material
  7. customPurification

Sources & evidence

ORD record
ord-0af3edcd23204d618582a3bfe22d3955
Source dataset
uspto-grants-2010_06
Patent number
US07741360B2

Reaction notes

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