Carbon Dioxide → 1-(1,1-Dimethylethyl) 4-fluoro-2,3-dihydro-1H-indole-1,7-dicarboxylate

HRID 387312Notes

Reaction equation

HRID 387312 reaction equation
[Li]C(C)(C)C.Br[C:7]1[CH:8]=[CH:9][C:10]([F:23])=[C:11]2[C:15]=1[N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12]2.[C:24](=[O:26])=[O:25]>C1COCC1>[CH3:20][C:19]([O:18][C:16]([N:14]1[C:15]2[C:11](=[C:10]([F:23])[CH:9]=[CH:8][C:7]=2[C:24]([OH:26])=[O:25])[CH2:12][CH2:13]1)=[O:17])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 59332682HCID 59332682, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 667467151-(1,1-Dimethylethyl) 4-fluoro-2,3-dihydro-1H-indole-1,7-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.6 M tert-BuLi (1.2 mL, 1.92 mmol) was added to a solution of 1,1-dimethylethyl 7-bromo-4-fluoro-2,3-dihydro-1H-indole-1-carboxylate (260 mg, 0.92 mmol) in THF (52 mL) at −78 (bath temp). The reaction was stirred for 5 min, and dry ice (CO2) powder was added. The reaction was stirred for 10 min, and was allowed to warm slowly to room temperature. The reaction mixture was washed with EtOAc, and the organic layer was evaporated. The crude product was purified by flash chromatography, giving the title compound.

Workup

  1. stirringThe reaction was stirred for 10 min
  2. washThe reaction mixture was washed with EtOAc
  3. customthe organic layer was evaporated
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-66ef7018d29b49808433b2340f3dcc87
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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