Dichloromethane → HCID 58215719, compound

HRID 593673Notes

Reaction equation

HRID 593673 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:14]=[C:15]([C:19]2[N:20]([CH3:30])[C:21]3[C:26]([C:27]=2[C:28]#[N:29])=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]=[N:17][CH:18]=1.O.NN.ClCCl>C(O)C>[NH2:3][CH2:12][C:13]1[CH:14]=[C:15]([C:19]2[N:20]([CH3:30])[C:21]3[C:26]([C:27]=2[C:28]#[N:29])=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 58215609HCID 58215609, compound

Product 1

HCID 58215719HCID 58215719, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-pyridin-3-yl]-1-methyl-1H-indole-3-carbonitrile (200 mg, 0.51 mmol) in ethanol (15 mL) is added hydrazine hydrate (327 mg, 10.2 mmol). The mixture is stirred at room temperature overnight. The reaction mixture is poured into dichloromethane (100 mL) and extracted with 1M HCl in water. The combined aqueous phase is basified with 5M NaOH in water and extracted with dichloromethane. The combined organic phase is dried over Na2SO4 and concentrated in vacuo to give 2-(5-aminomethyl-pyridin-3-yl)-1-methyl-1H-indole-3-carbonitrile, which is used in the next step without further purification. MS (ESI) m/z 263.27 (M+H)+.

Workup

  1. extractionextracted with 1M HCl in water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phase is dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f42d309b3fc84fc5bd376ef86411f18e
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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