4-tert-Butylphenol → HCID 23521733, compound

HRID 392437Notes

Reaction equation

HRID 392437 reaction equation
I[C:2]1[CH:3]=[C:4]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([O:32][C:2]2[CH:3]=[C:4]([N:9]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=2[CH3:8])=[CH:30][CH:31]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 73934-tert-ButylphenolHCID 23521705HCID 23521705, compound

Product 1

HCID 23521733HCID 23521733, compound

Procedure

The title compound was prepared following Example 342 using N-(3-iodo-4-methylphenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine and 4-tert-butylphenol and purifying via radial chromatography eluting with 50:50 to 53:47 THF/hexanes gave the title compound. 1H NMR (400 MHz) 1.32 (9H, s), 1.39 (3H, t, J=7.8 Hz), 2.19 (3H, s), 3.07 (2H, q, J=7.8 Hz), 4.79 (2H, s), 6.70 (3H, m), 6.92 (1H, dd, J=2.0, 7.8 Hz), 7.16 (1H, d, J=7.8 Hz), 7.20-7.31 (3H, m), 7.67 (1H, d, J=8.3 Hz), 8.31 (1H, bs), 8.50 (1H, bs). HRMS calculated 439.2055 [M+H]+ Found 439.2073.

Workup

  1. customThe title compound was prepared
  2. custompurifying via radial chromatography
  3. washeluting with 50:50 to 53:47 THF/hexanes

Sources & evidence

ORD record
ord-3aeb3625ca064fad9297556cacaf53b4
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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