Sodium Iodide → Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 857338Notes

Reaction equation

HRID 857338 reaction equation
CC#N.[Na+].[I-].C[Si](Cl)(C)C.[Br:11][C:12]1[C:13]2[CH:14]=[C:15]3[C:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])(O)[CH2:23][CH2:22][N:16]3[C:17]=2[CH:18]=[C:19]([F:21])[CH:20]=1.C([O-])(O)=O.[Na+]>CCOCC>[Br:11][C:12]1[C:13]2[CH:14]=[C:15]3[CH:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH2:22][N:16]3[C:17]=2[CH:18]=[C:19]([F:21])[CH:20]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 73553839Methyl 2-(8-bromo-6-fluoro-1-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 11267347Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To dry CH3CN (2.3 g, 56 mmol) at r.t. was added NaI (8.4 g, 56 mmol) and trimethylsilyl chloride (6.1 g, 56 mmol). Then a solution of the alcohol of Step 7 (1.9 g, 5.6 mmol) in Et2O (60 mL) was slowly added. The reaction mixture was stirred for 5 minutes at r.t. and poured into a 1:1 mixture of saturated aqueous NaHCO3/10% aqueous Na2S2O3 (100 mL) at 0° C. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The desired compound was obtained as a brown solid (1.3 g).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-827d54b68cbd4201a18ff1193480fd18
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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