Oxalyl chloride → HCID 21950065, compound

HRID 1819677Notes

Reaction equation

HRID 1819677 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13].C([O-])(O)=[O:18].[Na+]>CCOCC>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:15])[C:12]([OH:18])=[O:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 6764936-Bromoindole

Product 1

HCID 21950065HCID 21950065, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Step E (1): To a solution of 6-bromo-1H-indole (1.4 g, 7.14 mmol) in Et2O (15.0 mL) was added oxalyl chloride (1.18 g, 9.29 mmol) dropwise at 0° C. under N2. The reaction mixture was stirred at rt for 4 h. An orange precipitate formed, then 40 mL of saturated NaHCO3 was added. The mixture was then stirred at 80° C. for 30 min. Et2O was added to extract the unreacted starting materials. The resulting aqueous layer was acidified with concentrated HCl, and the product precipitated. The solid was filtered and dried to give 1.6 g (yield 83.6%) of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetic acid. MS (ESI) (M−H)+=265.98. 1H-NMR(500 MHz, CD3OD) δ 8.39-8.78 (m, 1 H), 8.21 (d, J=8.24 Hz, 1 H), 7.69 (s, 1 H), 7.40 (d, J=8.55 Hz, 1 H).

Workup

  1. customAn orange precipitate formed
  2. stirringThe mixture was then stirred at 80° C. for 30 min
  3. extractionto extract the
  4. customthe product precipitated
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-5bd90c1c63cc4a58b36ed8a8b37aa753
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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