Benzyl Bromide → Benzyl 5-methyl-2-indolecarboxylate

HRID 844431

Reaction equation

HRID 844431 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.C1CCN2C(=NCCC2)CC1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:12])=[CH:5]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2591885-methyl-1H-indole-2-carboxylic acid

Product 1

HCID 22612640Benzyl 5-methyl-2-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.43 g of 5-methyl-2-indolecarboxylic acid are dissolved in 15 ml of DMF; 2.11 g of DBU are added and the mixture is then left stirring for 1 hour at RT. 2.61 g of benzyl bromide are added dropwise and the mixture is then left stirring for 6 hours at RT. This 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. It is dried over Na2SO4 and then concentrated. The residue crystallizes from pentane and 3.3 g of the expected compound are obtained: m.p.=150-152° C.

Workup

  1. waitthe mixture is then left
  2. waitthe mixture is then left
  3. stirringstirring for 6 hours at RT
  4. concentrationThis mixture is concentrated under vacuum
  5. washwashed with water, with saturated Na2CO3 solution, with sulphate buffer
  6. dry with materialIt is dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue crystallizes from pentane and 3.3 g of the expected compound
  9. customare obtained

Sources & evidence

ORD record
ord-9b775c3404d04c898b6e568c3d3f402e
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Linked notes

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