Carbon Dioxide → HCID 68109550, compound

HRID 2179378Notes

Reaction equation

HRID 2179378 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1.C([Mg]Cl)(C)C.[C:28](=[O:30])=[O:29]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:28]([OH:30])=[O:29])[C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 68109080HCID 68109080, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 68109550HCID 68109550, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step C (300 mg, 0.62 mmol) in tetrahydrofuran (1.5 mL) was added isopropylmagnesium chloride (1 M in tetrahydrofuran) (0.75 mL, 0.75 mmol) dropwise under an argon atmosphere at −20° C. over 5 min. The reaction mixture was stirred at −15° C. to −10° C. for 1 h before dry CO2 gas was bubbled through the reaction mixture over 15 min. The reaction mixture was slowly allowed to reach to ambient temperature and stirred overnight. The mixture was quenched with aqueous saturated ammonium chloride solution (10 mL) and extracted with dichloromethane. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to give 8-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-6-carboxylic acid (125 mg, 50%) as a white solid. The crude product was directly used for the next step.

Workup

  1. customwas bubbled through the reaction mixture over 15 min
  2. customto reach to ambient temperature
  3. customThe mixture was quenched with aqueous saturated ammonium chloride solution (10 mL)
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9fcef0d01f541f9b5525141e27f82e7
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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