Dimethylformamide → HCID 68719600, compound

HRID 921975Notes

Reaction equation

HRID 921975 reaction equation
CC(C)CC(C1C=C2C(=CC=1)NC(C(O)=O)=C2)=O.CN(C=O)C.[CH2:24]([O:26][C:27]([C:29]1[NH:30][C:31]2[C:36]([C:37]=1Br)=[CH:35][C:34]([C:39](=[O:44])[CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:33][CH:32]=2)=[O:28])[CH3:25].C([O-])=O.[NH4+]>[Pd].O>[CH2:24]([O:26][C:27]([C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][C:34]([C:39](=[O:44])[CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:33][CH:32]=2)=[O:28])[CH3:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 2723923Ammonium formateHCID 68719603HCID 68719603, compoundHCID 68720944HCID 68720944, compound

Product 1

HCID 68719600HCID 68719600, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Synthesis of 5-(3-Methyl-butyryl)-1H-indole-2-carboxylic acid. DMF (5 mL) and water (0.625 mL) are added to the mixture of 3-Bromo-5-(3-methyl-butyryl)-1H-indole-2-carboxylic acid ethyl ester (408 mg, 1.1 mmol), ammonium formate (110 mg, 1.7 mmol), and 10% Pd/C (200 mg). The mixture is slightly shaken at room temperature for 70 minutes and then filtered through celite. The solvent is evaporated under vacuum to give 5-(3-Methyl-butyryl)-1H-indole-2-carboxylic acid ethyl ester as light yellow liquid as crude product with the purity of 90%; EI-MS m/z 274.1 (M++H). The crude ethyl ester is dissolved in dioxane (10 mL), then a solution of LiOH.H2O (195 mg, 4.6 mmol) in water (5 mL) is added to the flask. The mixture is stirred at room temperature for 2 days. Dioxane is stripped under vacuum. 10 mL water is added and extracted with CH2Cl2. The aqueous phase is then acidified with 6N HCl and extracted with CH2Cl2. The CH2Cl2 phase is then washed with saturated brine and dried over anhydrous Na2SO4. Solvent is removed under vacuum to give 5-(3-Methyl-butyryl)-1H-indole-2-carboxylic acid (250 mg, 88% for two steps) as white solid. EIMS m/z 246.1 (M++H).

Workup

  1. filtrationfiltered through celite
  2. customThe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-eb191e0c567e49799358ba11b872b189
Source dataset
uspto-grants-2016_03
Patent number
US09278089B2

Reaction notes

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