Chlorosuccinimide → HCID 89535667, compound

HRID 2278347Notes

Reaction equation

HRID 2278347 reaction equation
COC(=O)CC[S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:11][CH:10]=1)(=[O:8])=[O:7].C[O-].[Na+].C1C(=O)N([Cl:36])C(=O)C1>C1COCC1>[Cl:36][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:11][CH:10]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 10942334Sodium MethoxideHCID 117628758HCID 117628758, compound

Product 1

HCID 89535667HCID 89535667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 6-[(3-methoxy-3-oxopropyl)sulfonyl]-1H-indole-1-carboxylate (400 mg, 1.13 mmol) in THF (5.5 mL) was added sodium methoxide (2.26 mL, 0.5 M, 1.13 mmol). The reaction mixture was stirred for 20 minutes, then the solvents were removed under reduced pressure and the residue was stripped down from heptanes to generate a white foam. This foam was suspended in DCM (5.5 mL) at 0° C. and then NCS (151 mg, 1.13 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was quenched by the addition of brine (4 mL) and the phases were separated using a phase separator. The aqueous layer washed with DCM. The combined organics were concentrated under reduced pressure. The crude was purified on silica gel eluting with hexanes and ethyl acetate to afford the title compound.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customwas suspended in DCM (5.5 mL) at 0° C.
  3. stirringthe reaction mixture was stirred for 1 hour
  4. customThe reaction was quenched by the addition of brine (4 mL)
  5. customthe phases were separated
  6. washThe aqueous layer washed with DCM
  7. concentrationThe combined organics were concentrated under reduced pressure
  8. customThe crude was purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-24c6844373534f0ebbd775e29e3de069
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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