Carbon Dioxide → HCID 70561363, compound

HRID 1477842Notes

Reaction equation

HRID 1477842 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[C:11]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:12]=[C:13]([F:16])[CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[Li]CCCC.[C:32](=[O:34])=[O:33]>C1COCC1>[C:20]([O:19][C:18]([NH:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[C:15]2[C:10]=1[CH:9]=[CH:8][N:7]2[CH:6]([C:5]1[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:32]([OH:34])=[O:33])=[O:24])([CH3:22])([CH3:23])[CH3:21]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 70564826HCID 70564826, compoundHCID 178418339Butyllithium

Product 1

HCID 70561363HCID 70561363, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To the mixture of tert-butyl 1-(4-chlorobenzyl)-6-fluoro-1H-indol-4-ylcarbamate (8 g, 0.021 mol) in THF (300 mL) was added dropwise BuLi (2.5 M, 34 mL, 0.084 mol) at −78° C. and the mixture was stirred for another 30 min at −78° C. An excess of dry ice was added and the solution was warmed slowly to room temperature. The resulting mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The aqueous layer was extracted with EA and washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuo to afford the title compound (8 g, yield 89%). LC/MS m/z=363.1 [M-tBu+H]+.

Workup

  1. temperaturethe solution was warmed slowly to room temperature
  2. customThe resulting mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. extractionThe aqueous layer was extracted with EA
  4. washwashed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74d23dcff78c46648a33adac2d390e24
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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