Ethyl chloroformate → HCID 58190515, compound

HRID 589158Notes

Reaction equation

HRID 589158 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12](O)=[O:13])=[CH:7][CH:6]=2.C(OC(Cl)=O)C.[BH4-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][OH:13])=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 178503473-Bromoquinoline-6-carboxylic acid

Product 1

HCID 58190515HCID 58190515, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-bromoquinoline-6-carboxylic acid (1.32 g, 5.24 mmol) and TEA (876 uL, 6.29 mmol) in THF (30 mL) was added EtOCOCl (599 uL, 6.29 mmol) at 0° C. and stirred for 30 min. Then, a solution of NaBH4 (793 mg, 21.0 mmol) in H2O (6 mL) was added at the same temperature. The resulting reaction mixture was stirred at 0° C. for 30 min before being warmed to it and stirred overnight. THF was removed. The residue was diluted with H2O, acidified with 4 N HCl, then neutralized with NaHCO3, extracted with EtOAc, and purified by a SiO2 column (0-50% EtOAc/Hexanes, Rf=0.35 in 50% EtOAc) to afford the titled compound as a colorless oil (220 mg).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 0° C. for 30 min
  3. temperaturebefore being warmed to it
  4. stirringstirred overnight
  5. customTHF was removed
  6. additionThe residue was diluted with H2O
  7. extractionextracted with EtOAc
  8. custompurified by a SiO2 column (0-50% EtOAc/Hexanes, Rf=0.35 in 50% EtOAc)

Sources & evidence

ORD record
ord-1b75ef8e92ab4d2281696a6c7fe47f7d
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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