Acetic Acid → HCID 68747834, compound

HRID 1864788Notes

Reaction equation

HRID 1864788 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28]3[CH:29]=[C:30]([CH:34]=O)[CH:31]=[N:32][CH:33]=3)=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.[CH3:36][N:37]([CH3:41])[CH2:38][CH2:39][NH2:40]>ClCCCl>[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28]3[CH:29]=[C:30]([CH2:34][NH:40][CH2:39][CH2:38][N:37]([CH3:41])[CH3:36])[CH:31]=[N:32][CH:33]=3)=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 86616467HCID 86616467, compound

Product 1

HCID 68747834HCID 68747834, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (855 mg, 4.05 mmol) and then enough acetic acid to bring the pH to 5 were added to a solution of 5-(1H-indol-5-yl)-pyridine-3-carbaldehyde (300 mg, 1.35 mmol) and N,N-dimethylethylene diamine (237 mg, 2.7 mmol) in 15 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature for 48 h, and then the volatiles were removed in the presence of celite. The product was eluted from the celite through silica gel (elution with methanol/dichloromethane) to give 328 mg of product. LC/MS: Retention time, 0.43 min; (M+H)=295.19.

Workup

  1. customthe volatiles were removed in the presence of celite
  2. washThe product was eluted from the celite through silica gel (elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-7d513fe75b2d47ba8182f9567bc6b903
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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