Sodium Carbonate → HCID 22722267, compound

HRID 1581719Notes

Reaction equation

HRID 1581719 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])([O-:3])=[O:2].C1C=C[NH+]=CC=1.Br[Br-]Br.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>C1COCC1.C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[C:7]2[CH2:13][CH2:14][N:15]1[C:16](=[O:25])[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]1=[O:24])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 227222762-[2-(5-Nitro-1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 22722267HCID 22722267, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21956068Chloroform tetrahydrofuranSolvent

Procedure

2-[2-(5-Nitro-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione (1 mmol) is dissolved in THF/chloroform (1:1) and treated with pyridine hydrobromide perbromide at 0° C. for 90 min, then eluted from a silica column with chloroform-methanol. The product is dissolved in toluene-ethanol (1:1) and treated with phenylboronic acid (1.5 equiv), sodium carbonate (2.5 equiv), lithium chloride (3 equiv), and palladium tetrakis(triphenylphosphine) (5 mol %). The mixture is refluxed 4 h, concentrated in vacuo, and the oil chromatographed on silica eluted with ethyl acetate-hexane to afford 2-[2-(5-nitro-2-phenyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione. This compound is dissolved in ethanol (6 mL) and refluxed with ethylenediamine (3 equiv) 18 h. The solvent is removed in vacuo and the material acetylated with pyridine-acetic anhydride (1:1, 6 mL). The solvent is removed in vacuo and the residue chromatographed on silica eluted with ethyl acetate-hexane. This product is hydrogenated and transformed to the carbamic acid methyl ester as in the example above. Purified product is isolated by reverse-phase HPLC.

Workup

  1. washeluted from a silica column with chloroform-methanol
  2. dissolutionThe product is dissolved in toluene-ethanol (1:1)
  3. temperatureThe mixture is refluxed 4 h
  4. concentrationconcentrated in vacuo
  5. customthe oil chromatographed on silica
  6. washeluted with ethyl acetate-hexane

Sources & evidence

ORD record
ord-34a08ec6f5234cf9b7b024365912a36e
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

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