Indole → HCID 69026414, compound

HRID 1866799Notes

Reaction equation

HRID 1866799 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[SH:18])[CH3:8])([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)CCC1=O.S(Cl)Cl.[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32]1.C(=O)(O)[O-].[Na+]>C1COCC1.ClCCCl>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[S:18][C:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:31][CH:32]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 798IndoleHCID 25353Sulfur dichlorideHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 69023513HCID 69023513, compound

Product 1

HCID 69026414HCID 69026414, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

[2-(5-Fluoro-2-mercapto-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (240 mg, 0.84 mmol) is dissolved in dry THF (3 mL) and added dropwise to a solution of N-chlorosuccinimide (112 mg, 0.84 mmol) in 1,2-dichloroethane (3 mL) at 0° C. The mixture is allowed to heat to ambient temperature and is stirred for 30 minutes. The resulting sulfenyl chloride solution is added dropwise to a solution of 1H-indole (147 mg, 1.26 mmol) in dry THF (3 mL) at 0° C. The mixture is stirred for 15 minutes at 0° C. before adding saturated sodium bicarbonate solution (15 mL). The mixture is extracted with ethyl acetate (3×20 mL) and the combined organic fractions are washed with brine, dried (MgSO4) and concentrated in vacuo. The product is purified by silica gel chromatography eluting with ethyl acetate-heptane, first (1:10) then (1:4). Upon evaporation of the volatiles 99 mg (29%) of the title compound is isolated.

Workup

  1. stirringThe mixture is stirred for 15 minutes at 0° C.
  2. extractionThe mixture is extracted with ethyl acetate (3×20 mL)
  3. washthe combined organic fractions are washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe product is purified by silica gel chromatography
  7. washeluting with ethyl acetate-heptane, first (1:10)
  8. customUpon evaporation of the volatiles 99 mg (29%) of the title compound
  9. customis isolated

Sources & evidence

ORD record
ord-dfcc20dff5cc4d67a57fcdef08075160
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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