Ethyl Acetate → HCID 69078396, compound

HRID 1510225Notes

Reaction equation

HRID 1510225 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19](O)=[O:20].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:19](=[O:20])[CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 2724699PyBOPHCID 34115665-Bromoindoline

Product 1

HCID 69078396HCID 69078396, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromoindoline (5.0 g), 2-pyridinylacetic acid hydrochloride (4.82 g) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (15.8 g) in N,N-dimethylformamide (100 mL) was added dropwise diisoprpylethylamine (6.53 g) at ambient temperature and the mixture was stirred at the same temperature for 20 hours. The mixture was poured into a mixture of ethyl acetate and water and the separated organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 5-bromo-1-(2-pyridinylacetyl)indoline (5.23 g) as a light-brown powder.

Workup

  1. washthe separated organic layer was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-970c954ff3404700b208e6bf758fd739
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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