Triethylamine → HCID 3727093, compound

HRID 1172989Notes

Reaction equation

HRID 1172989 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH:15]=O.C([BH3-])#N.[Na+].C(N(CC)CC)C>CO.[Cl-].[Zn+2].[Cl-]>[NH:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10328IndolineHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 3727093HCID 3727093, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of indoline (0.20 g, 1.68 mmol) in methanol (15 ml) were added sequentially imidazole-2-carboxaldehyde (0.24 g, 2.52 mmol), zinc chloride (0.92 g, 6.71 mmol) and sodium cyanoborohydride (0.32 g, 5.03 mmol). The reaction mixture was shaken at 50° C. for 16 hours, then triethylamine (0.5 ml) was added and the mixture shaken for a further 5 min. The resulting suspension was filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: methanol/dichloromethane gradient) to yield the title compound as an off-white solid (0.17 g, 52%); MS (ISP): 200.3 ([M+H]+).

Workup

  1. stirringthe mixture shaken for a further 5 min
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (eluant: methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-01fac55936674772b4fa5dbedde06e41
Source dataset
uspto-grants-2010_11
Patent number
US07834044B2

Reaction notes

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