Morpholine → (5-bromo-1H-indole-2-yl)(morpholino)methanone

HRID 1820367Notes

Reaction equation

HRID 1820367 reaction equation
[Br: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)=[CH:5]2.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:13])=[CH:5]2

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 2521375-Bromo-1H-indole-2-carboxylic acid

Product 1

HCID 47154711(5-bromo-1H-indole-2-yl)(morpholino)methanoneYield 103.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromoindole-2-carboxylic acid (5 g, 21 mmol), and 1,1′-carbonyldiimidazole (4.39 g, 27 mmol) in tetrahydrofuran (60 mL) was stirred at room temperature overnight. Morpholine (3.63 mL, 42 mmol) was added and the mixture was stirred for an additional 40 min. The reaction mixture was partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate. The organic layer was washed with hydrochloric acid (1N) and brine, then dried over sodium sulfate, filtered and evaporated in vacuo, to give 6.74 g (99%) of the desired compound as a yellow solid which was used without further purification.

Workup

  1. stirringthe mixture was stirred for an additional 40 min
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with hydrochloric acid (1N) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e41716076443478989c9cd5b92018f8a
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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