Benzyl Bromide → Benzyl 4-methoxyindole-2-carboxylate

HRID 844432Notes

Reaction equation

HRID 844432 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([OH:14])=[O:13])[NH:7]2.C1CCN2C(=NCCC2)CC1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([O:14][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:13])[NH:7]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9072484-Methoxy-1H-indole-2-carboxylic acid

Product 1

HCID 22612550Benzyl 4-methoxyindole-2-carboxylateYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.65 g of 4-methoxyindole-2-carboxylic acid are dissolved in 15 ml of DMF, 2.11 g of DBU are added and the mixture is then stirred at RT for 1 hour. 2.61 g of benzyl bromide are added dropwise at RT and this mixture is stirred for 5 hours at RT. The mixture is concentrated under vacuum and the residue is taken up in EtOAc, washed with water, with saturated Na2CO3 solution, with sulphate buffer and then with saturated aqueous NaCl. This solution is dried over Na2SO4 and concentrated. 3.57 g of the expected compound are obtained, which product crystallizes from pentane: m.p.=162-164° C.

Workup

  1. stirringthis mixture is stirred for 5 hours at RT
  2. concentrationThe mixture is concentrated under vacuum
  3. washwashed with water, with saturated Na2CO3 solution, with sulphate buffer
  4. dry with materialThis solution is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-196f7f07ac614cc8ab79c8a4b4d19a87
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

Loading…