Triethylamine → 7-Methyl-1H-indole-5-carboxylic acid

HRID 1976789Notes

Reaction equation

HRID 1976789 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([CH3:16])[CH:15]=1)[NH:12][CH:11]=[CH:10]2)(=O)=O.C(N(CC)CC)C.C1[CH2:30][O:29]CC1.[OH2:31]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH3:16][C:14]1[CH:15]=[C:7]([C:30]([OH:29])=[O:31])[CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21881883Oxolane--water (1/1)HCID 21998738HCID 21998738, compound

Product 1

HCID 152475557-Methyl-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

A solution of 7-methyl-5-indolyl trifluoromethanesulfonate (3.19 g, 11.4 mmol), triethylamine, and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (catalytic)in 9:1 THF/water was stirred under CO2 (500 psi) until HPLC indicated complete conversion. The solution was treated with water (30 mL), adjusted to pH 4-5, and extracted sequentially with ethyl acetate (100 mL) and dichloromethane (3×40 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product which was used in the next step without further purification.

Workup

  1. extractionextracted sequentially with ethyl acetate (100 mL) and dichloromethane (3×40 mL)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-851d473653a544a0aa7a3560d6a62891
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

Loading…