Hydrochloric Acid → HCID 59277605, compound

HRID 1362450Notes

Reaction equation

HRID 1362450 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][C:6](C(O)=O)=[C:5]2[CH3:15].BrC1C(C)=C2C(=CC=1)NC(C(O)=O)=C2C.CCOCC.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][CH:6]=[C:5]2[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59277568894853-35-1HCID 66967595HCID 66967595, compound

Product 1

HCID 59277605HCID 59277605, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
240 °C

Procedure

A 1:1 mixture of 5-bromo-3,6-dimethyl-1H-indole-2-carboxylic acid and 5-bromo-3,4-dimethyl-1H-indole-2-carboxylic acid (4.39 g, 16.4 mmol) in quinoline (10 mL) with copper powder (250 mg) was stirred at 240° C. for 3 h to give the corresponding mixture of the decarboxylated products. Upon cooling, ether (200 mL) was added and the mixture acidified with 5N HCl. The layers were separated, the organics were washed with brine, dried and evaporated. Chromatography (silica, 15% CH2Cl2 in hexane) and crystallization from a CH2Cl2/hexane mixture afforded the title compound (1.35 g 37%). 1H NMR (300 MHz, CDCl3) 7.74 (s, 1H), 7.21 (is, 1H), 6.90 (s, 1H), 2.48 (s, 3H), 2.27 (s, 3H).

Workup

  1. customto give
  2. additionthe corresponding mixture of the decarboxylated products
  3. temperatureUpon cooling
  4. customThe layers were separated
  5. washthe organics were washed with brine
  6. customdried
  7. customevaporated
  8. customChromatography (silica, 15% CH2Cl2 in hexane) and crystallization from a CH2Cl2/hexane mixture

Sources & evidence

ORD record
ord-255ae0c9aab94222b5bd4ebd66444e8d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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