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

HRID 723190Notes

Reaction equation

HRID 723190 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[C:11]([O:15][C:16](=[O:37])[NH:17][C:18]([C:20]1[S:21][C:22]([S:35][CH3:36])=[C:23]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30](Br)[CH:29]=2)(=[O:27])=[O:26])[CH:24]=1)=[NH:19])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[C:11]([O:15][C:16](=[O:37])[NH:17][C:18]([C:20]1[S:21][C:22]([S:35][CH3:36])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=3)[CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:24]=1)=[NH:19])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857649tert-butyl N-[4-[3-(3-aminophenyl)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-amino-phenyl boronic acid (27 mg, 0.2 mmol), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.1 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosine)palladium(0) (29 mg, 0.025 mmol, Strem Chemicals Inc, Newburyport, Mass.), Na2CO3 (400 μL, 2M), and toluene/EtOH mixture (2:1, 1.2 mL) afforded 35 mg (70%) after purification (SiO2, flash elution: 30% EtOAc in hexanes) of the title compound as a white foam. ESI-MS (m/z): Calcd. for C23H25N3O4S3: 503.6; found: 503.9, 404.1 (M−Boc).

Workup

  1. customafforded 35 mg (70%)
  2. customafter purification (SiO2, flash elution: 30% EtOAc in hexanes) of the title compound as a white foam

Sources & evidence

ORD record
ord-c8fdb17842554ca3924690d0b9d487d5
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…