HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Carbon Dioxide → 1-{[(1,1-Dimethylethyl)oxy]carbonyl}-4-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

HRID 656073
Notes
Print preview

Reaction equation

HRID 656073 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 667467151-{[(1,1-Dimethylethyl)oxy]carbonyl}-4-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

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-325f3d02d0784d7e854215ac3917b7e6
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071584B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes