Dimethylformamide → HCID 11516200, compound

HRID 2250530Notes

Reaction equation

HRID 2250530 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:16]=[CH:17][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2([CH3:13])[CH3:12].ClS([N:30]=[C:31]=O)(=O)=O.CN(C=O)C>C(OCC)(=O)C>[C:31]([C:16]1[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([C:4]2[CH:5]=[C:6]3[C:10](=[C:2]([F:1])[CH:3]=2)[NH:9][C:8](=[O:11])[C:7]3([CH3:13])[CH3:12])=[CH:18][CH:17]=1)#[N:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 11580988HCID 11580988, compound

Product 1

HCID 11516200HCID 11516200, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of tert-butyl 2-(7-fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1H-pyrrole-1-carboxylate (1.0 g, 2.9 mmol) was added chlorosulfonylisocyanate (0.28 mL, 3.2 mmol). The mixture was stirred at 25° C. for 2 h then DMF (0.21 mL, 2.9 mmol) was added and the mixture was stirred for an additional 1 h. The mixture was diluted with ethyl acetate and washed with NaHCO3, water, saturated aqueous NaCl, dried over MgSO4, and concentrated. Flash chromatography (2% MeOH/CH2Cl2) afforded 0.23 g (21%) of the title compound as a white solid.

Workup

  1. stirringthe mixture was stirred for an additional 1 h
  2. washwashed with NaHCO3, water, saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0f9399a22bb4b4d8a6b576d21864231
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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