4-Iodo-2-methoxynicotinaldehyde → HCID 59762244, compound

HRID 929122Notes

Reaction equation

HRID 929122 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:5]2=[O:23].IC1C(C=O)=C(OC)N=CC=1>CO.CC(O)=O.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:14])[N:6]([CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:5]2=[O:23]

Participants

5

Reactant 2

HCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 59761748HCID 59761748, compound

Product 1

HCID 59762244HCID 59762244, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
80 °C

Procedure

Pd/C (250 mg) was added to a solution of crude 5-amino-6-nitro-2-(3-(pyrrolidin-1-yl)propyl)isoindoline-1,3-dione in MeOH/AcOH (100 mL/5 mL) and hydrogenated for 5 h. The mixture was filtered through Celite and the filtrate was treated with 4-iodo-2-methoxynicotinaldehyde (3.2 g, 12.07 mmol) and stirred at ambient temperature open to air for 12 h and at 80° C. for 5 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo to dryness. Purification by flash chromatography gave the title 5,6-diamino-2-(3-(pyrrolidin-1-yl)propyl)isoindoline-1,3-dione as a solid (2.02 g, 32% through 4 steps). 1H NMR (MeOD): δ 8.15 (s, 2H), 8.01-8.08 (t, J=3 Hz 1H), 7.64 (t, J=3 Hz, 1H), 3.89-3.78 (m, 2H), 3.41-3.22 (m, 2H), 2.95-2.81 (m, 6H), 2.15-1.82 (m, 7H). ESMS (m/z) 532 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. concentrationconcentrated in vacuo to dryness
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6aaec075fd8a44bf9f781a7c526a4f43
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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