Lithium Carbonate → HCID 21196126, compound

HRID 1066858Notes

Reaction equation

HRID 1066858 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[Cl:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][CH2:12][C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Li+].[Li+]>C(OCC)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[C:3](=[O:4])[CH2:2][Br:1])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 61147Bromoacetyl bromideHCID 21196037HCID 21196037, compound

Product 1

HCID 21196126HCID 21196126, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

Under a nitrogen atmosphere bromoacetylbromide (1.31 ml, 0.015 mol) was added to a slurry of 2-[4-chlorophenoxymethyl]-1H-indole (0.81 g, 0.003 mol), and lithium carbonate (2.22 g, 0.03 mol) in diethyl ether (37.5 ml). The resulting mixture was heated to 55° C. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between diethyl ether and a sodium bicarbonate solution. The organic fraction was washed with water and then brine, and then dried over sodium sulfate. The solvents were removed in vacuo. Yield: 1.34 g. NMR was consistent with the proposed title structure.

Workup

  1. customThe reaction mixture was partitioned between diethyl ether
  2. washThe organic fraction was washed with water
  3. dry with materialbrine, and then dried over sodium sulfate
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-67ae0ecfb3b74363ba4ddab8616fd771
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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