Sodium Hydroxide → HCID 22310831, compound

HRID 967097Notes

Reaction equation

HRID 967097 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:22][C:21]2[CH:24]=[CH:25][C:26]([Cl:27])=[C:19]([Cl:18])[CH:20]=2)[C:5]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Product 1

HCID 22310831HCID 22310831, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Powdered sodium hydroxide (0.5 g) was added in a single portion to a vigorously stirred solution of ethyl 3-bromoindole-2-carboxylate (0.3 g), 3,4-dichlorobenzyl bromide (0.32 g) and tetra-n-butylammonium hydrogensulphate (50 mg) in dichloromethane. The reaction was stirred for 3 hours then partitioned between 2M HCl and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-5% ethyl acetate as eluent to give the desired end product as a colourless oil (0.35 g, 73%); NMR δ (CDCl3) 1.42 (t, 3H), 4.41 (q, 2H), 5.73 (s, 2H), 6.84 (d, 1H), 7.18-7.40 (m, 5H), 7.74 (d, 11H); M/z (+) 428 (MH+), 426, 346, 159.

Workup

  1. customthen partitioned between 2M HCl and ethyl acetate
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-b6e7c95a9b144358930910349a349ffd
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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