tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate → HCID 86654872, compound

HRID 1964133Notes

Reaction equation

HRID 1964133 reaction equation
[CH:1]1([C:6]2[CH:34]=[CH:33][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=[C:15](I)[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:35]([F:38])([F:37])[F:36])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:39]([Zn]CC)[CH3:40]>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:1]1([C:6]2[CH:34]=[CH:33][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=[C:15]([CH2:39][CH3:40])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:35]([F:38])([F:37])[F:36])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 67249572tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateHCID 178418750HCID 178418750, compound

Product 1

HCID 86654872HCID 86654872, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (17 mg, 0.027 mmol) in THF (0.500 mL) in a 0.5-2.0 mL heavy-walled microwave sealed tube under N2 was added diethylzinc (0.074 mL, 0.037 mmol) and bis(tri-t-butylphosphine)palladium(0) (1.223 mg, 2.393 μmol). The reaction was then heated to 70° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3, filtered by vacuum filtration through Celite®, and washed with EtOAc (2×5 mL). The filtrate was then extracted with EtOAc (3×5 mL). The organic layers were combined and washed with saturated NaCl (1×10 mL), dried (MgSO4), and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure. The residue was purified by preparative TLC to give the title compound (6.6 mg) as an amber oil. LCMS m/z=542.6 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. filtrationfiltered by vacuum filtration through Celite®
  3. washwashed with EtOAc (2×5 mL)
  4. extractionThe filtrate was then extracted with EtOAc (3×5 mL)
  5. washwashed with saturated NaCl (1×10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered by vacuum filtration through a glass fiber paper
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-af923d26e9e6488490a0a4579279a14a
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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