HCID 69293152, compound → HCID 69294521, compound

HRID 747827Notes

Reaction equation

HRID 747827 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[CH2:11][N:12]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[CH2:11][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 1

HCID 69293152HCID 69293152, compound

Product 1

HCID 69294521HCID 69294521, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd on carbon (10% wt, 1.01 g) was placed in a 100 mL flask purged with Ar and 40 mL of MeOH was added. 2-Nitro-5-chloro-1-[bis(2-pyridylmethyl)aminomethyl]-benzene (569 mg, 1.55 mmol) was dissolved in 10 mL of MeOH and added to the reaction flask with a syringe. A balloon with H2 was attached and the reaction was left to stir vigorously under H2 for 1 h at rt. The reaction was purged with Ar, filtered through Celite and dried to yield a brown solid (380 mg, 72%) that was used without further purification. The product can be purified by flash chromatography on basic Al2O3 (20:4:2.5 CH2Cl2:EtOAc:isopropylamine) to give a brown solid (65%). 1H NMR (CDCl3, 300 MHz) δ 3.59 (2H, s), 3.80 (4H, s), 6.52 (1H, d), 7.00 (2H, m), 7.11 (2H, m), 7.38 (2H, t), 7.60 (2H, 5), 8.55 (2H, d). 13C NMR (CDCl3, 300 MHz) δ 57.18, 58.71, 116.62, 121.28, 121.98, 123.20, 123.67, 127.91, 130.29, 136.39, 144.94, 148.64, 158.22. HRMS (ESI) calcd MH+, 339.1371; found, 339.1383.

Workup

  1. custompurged with Ar and 40 mL of MeOH
  2. additionwas added
  3. additionadded to the reaction flask with a syringe
  4. waitthe reaction was left
  5. customThe reaction was purged with Ar
  6. filtrationfiltered through Celite
  7. customdried

Sources & evidence

ORD record
ord-6726b112c462429e803f643a3ef3ac8e
Source dataset
uspto-grants-2008_07
Patent number
US07399639B2

Reaction notes

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