Ethyl chloroformate → HCID 86720579, compound

HRID 513207Notes

Reaction equation

HRID 513207 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)=[CH:9][N:8]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:7]=12.[Li+].CC([N-]C(C)C)C.Cl[C:41]([O:43][CH2:44][CH3:45])=[O:42]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:22])([F:24])[F:23])=[CH:16][CH:15]=3)=[C:9]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[N:8]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:7]=12

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 2724682Lithium diisopropylamideHCID 86720577HCID 86720577, compound

Product 1

HCID 86720579HCID 86720579, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of tert-butyl 7-chloro-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (349 mg, 0.76 mmol) in THF (15 mL) cooled to −78 C was added LDA (0.57 mL, 1.1 mmol, 2 M). After 30 min at this temperature, ethyl chloroformate (0.15 mL, 1.5 mmol) was added and the mixture was warmed to r.t. slowly. The reaction mixture was then quenched with 5% potassium bisulfate and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified on silica (gradient elution, 0-30% EtOAc/hexanes) to yield the title product (362 mg). HRMS (ESI) calc (M+H)+=529.1348. found 529.1346.

Workup

  1. customThe reaction mixture was then quenched with 5% potassium bisulfate
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified on silica (gradient elution, 0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9abbb1fb1d80490ba55dd808b855c17a
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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