N-Iodosuccinimide → tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515679Notes

Reaction equation

HRID 515679 reaction equation
[CH:1]1([C:6]2[CH:33]=[CH:32][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:16]5=[CH:15][C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:34]([F:37])([F:36])[F:35])[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:38]N1C(=O)CCC1=O>C(Cl)Cl>[CH:1]1([C:6]2[CH:33]=[CH:32][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[C:16]5=[C:15]([I:38])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:34]([F:37])([F:35])[F:36])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67248866tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 67249572tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (100 mg, 0.195 mmol) in DCM (2 mL) was added 1-iodopyrrolidine-2,5-dione (43.8 mg, 0.195 mmol) at 0° C. and the reaction was allowed to continue at 0° C. for 30 min in a 20 mL sealed scintillation vial. After 30 min, the reaction mixture was diluted with DCM, washed with water (3×10 mL), sodium thiolsulfate pentahydrate (aq) (2×10 mL), dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to give the title compound as an off-white solid (118 mg). LCMS m/z=640.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (s, 9H), 1.55-1.73 (m, 4H), 1.79-1.89 (m, 2H), 1.95-2.05 (m, 2H), 2.26-2.38 (m, 1H), 2.51-2.56 (m, 1H), 2.77-2.88 (m, 1H), 2.94 (dd, J=15.92, 3.41 Hz, 1H), 3.20-3.28 (m, 1H), 3.50-3.60 (m, 1H), 3.99-4.08 (m, 1H), 4.12-4.21 (m, 1H), 5.18 (s, 2H), 6.79 (d, J=2.27 Hz, 1H), 6.87 (dd, J=8.78, 2.46 Hz, 1H), 7.26 (d, J=8.84 Hz, 1H), 7.63 (d, J=8.59 Hz, 1H), 7.70-7.77 (m, 2H).

Workup

  1. customsealed scintillation vial
  2. waitAfter 30 min
  3. washwashed with water (3×10 mL), sodium thiolsulfate pentahydrate (aq) (2×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7803487d475241edb3d927399ed9f49f
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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