1,2-Dichloroethane → HCID 25204499, compound

HRID 1716854Notes

Reaction equation

HRID 1716854 reaction equation
[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][CH:19]=[C:20]([C:22](O)=[O:23])[N:21]=3)=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(Cl)CCl.[CH:29]1[CH:30]=CC2N(O)N=[N:35][C:33]=2[CH:34]=1.N1CCCC1>CN(C=O)C.CCOC(C)=O.O>[N:35]1([C:22]([C:20]2[N:21]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH2:10][N:1]4[C:9]5[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=5)[CH:3]=[CH:2]4)=[CH:12][CH:13]=3)[O:18][CH:19]=2)=[O:23])[CH2:30][CH2:29][CH2:34][CH2:33]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 57550226HCID 57550226, compound

Product 1

HCID 25204499HCID 25204499, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of 2-[4-(1H-indol-1-ylmethyl)phenyl]-1,3-oxazole-4-carboxylic acid (0.4 g, 1.26 mmol) in DMF was treated sequentially with EDC (0.29 g, 1.51 mmol), HOBt (0.186 g, 1.38 mmol) and pyrrolidine (0.098 g, 11.38 mol) was stirred at 80° C. overnight. The resultant residue was dissolved in EtOAc and water. The layers were separated and the aqueous layer was washed with EtOAC. The combined organic layers were washed successively with water, saturated sodium chloride, dried over Mg2SO4 and concentrated under reduced pressure to give a crude oil. The oil was purified by column chromatography (silica, MeOH:CH2Cl2 5%) to give the title product in 44% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 372 (MH+).

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with EtOAC
  3. washThe combined organic layers were washed successively with water, saturated sodium chloride
  4. dry with materialdried over Mg2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude oil
  7. customThe oil was purified by column chromatography (silica, MeOH:CH2Cl2 5%)

Sources & evidence

ORD record
ord-90dfd939dd474b489547ea3672653f73
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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