4-tert-Butylbenzaldehyde → HCID 86603116, compound

HRID 855432Notes

Reaction equation

HRID 855432 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][NH2:21])[CH:14]=1.[BH4-].[Na+].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][C:31]=2[C:33](O)=[O:34])[CH:26]=[CH:25]1.CCN=C=NCCCN(C)C.Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:21]([CH2:20][CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[C:33]([C:31]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:32]=2[NH:24][CH:25]=[CH:26]3)=[O:34])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 703244-tert-ButylbenzaldehydeHCID 742811H-Indole-7-carboxylic acidHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86603116HCID 86603116, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 61 mg (0.5 mmol) of 2-(3-pyridyl)-ethyl amine were dissolved in 2 ml methanol and the solution was stirred for 2 h at rt. 18.5 mg (0.5 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt for 30 min, the solvent was evaporated and the residue was suspended in 4 ml DCM. 88 mg (0.55 mol) of 1H-indole-7-carboxylic acid and 105 mg (0.55 mmol) of EDC.HCl were added and the mixture was stirred at rt over night. The product was purified by column chromatography (silica gel; diethyl ether) to yield 70 mg (34%) product as a colorless oil. MS (ISP) 412.4 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 30 min
  2. customthe solvent was evaporated
  3. stirringthe mixture was stirred at rt over night
  4. customThe product was purified by column chromatography (silica gel; diethyl ether)

Sources & evidence

ORD record
ord-55d5c46ebc2841799595325dde3abc1e
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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