Cyclamen aldehyde → HCID 66577251, compound

HRID 1512557Notes

Reaction equation

HRID 1512557 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH2:14])=[CH:4][CH:3]=1.[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([CH3:28])[CH:26]=O)=[CH:20][CH:19]=1)([CH3:17])[CH3:16].C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH:14][CH2:26][CH:25]([CH3:28])[CH2:24][C:21]2[CH:20]=[CH:19][C:18]([CH:15]([CH3:17])[CH3:16])=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517827Cyclamen aldehydeHCID 5003444Sodium cyanoborohydrideHCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Product 1

HCID 66577251HCID 66577251, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylamine (0.300 g, 1.19 mmol) and 3-(4-isopropylphenyl)isobutyraldehyde (0.272 g, 1.43 mmol) were combined in toluene (3 mL) and stirred at 110° C. for 1 hour. After cooling to room temperature, toluene was removed under vacuum and the mixture was diluted with THF (4 mL). Sodium cyanoborohydride (0.188 g, 2.98 mmol) was added, and the reaction was stirred at room temperature for 1 hour. The mixture was adsorbed onto silica gel and purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customtoluene was removed under vacuum
  3. additionthe mixture was diluted with THF (4 mL)
  4. stirringthe reaction was stirred at room temperature for 1 hour
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a5222da0d6474d1186e7daad42f6a554
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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