Hydrazine hydrate (1:1) → HCID 23152393, compound

HRID 1012358Notes

Reaction equation

HRID 1012358 reaction equation
[Br:1][C:2]1[N:3]([CH2:21][CH2:22][N:23]2C(=O)C3C(=CC=CC=3)C2=O)[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.O.NN>CO.O1CCCC1>[NH2:23][CH2:22][CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[Br:1]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23152709HCID 23152709, compound

Product 1

HCID 23152393HCID 23152393, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-bromo-3-cyclohexyl-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethyl]-1H-indole-6-carboxylate (3.96 g, 7.78 mmol) in methanol (50 ml) and tetrahydrofuran (30 ml) was added hydrazine monohydrate (1.88 ml, 38.7 mmol), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was filtered with celite and washed with ethyl acetate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=30:1-15:1) to give methyl 1-(2-aminoethyl)-2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (2.95 g, yield 100%).

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. washwashed with ethyl acetate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=30:1-15:1)

Sources & evidence

ORD record
ord-5a57242aea964661a3a99a20c28fb02a
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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