1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86711990, compound

HRID 1051348Notes

Reaction equation

HRID 1051348 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=O)[NH:6]2.[NH4+].[Cl-].CC[N:18]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([NH2:18])=[O:13])[NH:6]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 40355794-Fluoroindole-2-carboxylic acid

Product 1

HCID 86711990HCID 86711990, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 34 (179 mg, 1.00 mmol) in anhydrous DMF (2.0 mL) were added NH4Cl (160 mg, 3.00 mmol), EDCI (395 mg, 2.20 mmol), HOBt (297 mg, 2.20 mmol) and TEA (303 mg, 3.00 mmol) at RT. After stirring at RT for 3 h, the mixture was quenched with H2O (10 mL) the resulting mixture was extracted with EtOAc (3×6 mL). The combined extracts were dried and concentrated. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1 to 3:1) to afford 130 mg (73%) of 4-fluoro-1H-indole-2-carboxamide (36) as a white solid. LCMS (ESI) m/z: 179.1 [M+H]+.

Workup

  1. customthe mixture was quenched with H2O (10 mL) the resulting mixture
  2. extractionwas extracted with EtOAc (3×6 mL)
  3. customThe combined extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography
  6. washeluting with petroleum ether/EtOAc (5:1 to 3:1)

Sources & evidence

ORD record
ord-5f4fe5ce8bac4441bbaaf4967605efe4
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

Loading…