Sodium Carbonate → tert-butyl N-[4-[3-(4-hydroxy-2,6-dimethylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216151Notes

Reaction equation

HRID 2216151 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:18])[CH:5]=[C:6]([CH3:17])[C:7]=1B1OC(C)(C)C(C)(C)O1.[C:19]([O:23][C:24](=[O:45])[NH:25][C:26]([C:28]1[S:29][C:30]([S:43][CH3:44])=[C:31]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38](Br)[CH:37]=2)(=[O:35])=[O:34])[CH:32]=1)=[NH:27])([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[C:19]([O:23][C:24](=[O:45])[NH:25][C:26]([C:28]1[S:29][C:30]([S:43][CH3:44])=[C:31]([S:33]([C:36]2[CH:37]=[C:38]([C:7]3[C:6]([CH3:17])=[CH:5][C:4]([OH:18])=[CH:3][C:2]=3[CH3:1])[CH:39]=[CH:40][CH:41]=2)(=[O:35])=[O:34])[CH:32]=1)=[NH:27])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 218863883,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857620tert-butyl N-[4-[3-(4-hydroxy-2,6-dimethylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

Following the same procedure as in Example 1, step c, reaction of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (355 mg, 0.8 mmol, assuming quantitative yield from Example 224, step a), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (100 mg, 0.2 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosine)palladium(0) (58 mg, 0.05 mmol, Strem Chemicals Inc, Newburyport, Mass.), Na2CO3 (0.8 mL, 2M), and toluene/EtOH mixture (2:1, 2.4 mL) afforded 35 mg (13%) after purification (PTLC) of the title compound as a tan solid. ESI-MS (m/z): Calcd. for C25H28N2O5S3: 532.7; found: 532.8, 477.0, 433.1 (M−Boc).

Workup

  1. customafforded 35 mg (13%)
  2. customafter purification (PTLC) of the title compound as a tan solid

Sources & evidence

ORD record
ord-ca24f73f85e14b2389971a944e73a2e7
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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