Sodium Carbonate → tert-butyl N-[4-[3-(4-amino-2-methyl-6-nitrophenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216153Notes

Reaction equation

HRID 2216153 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH2:11])=[CH:4][C:3]=1[CH3:12].[C:13]([O:17][C:18](=[O:41])[NH:19][C:20]([C:22]1[S:23][C:24]([S:39][CH3:40])=[C:25]([S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=2)(=[O:29])=[O:28])[CH:26]=1)=[NH:21])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[C:13]([O:17][C:18](=[O:41])[NH:19][C:20]([C:22]1[S:23][C:24]([S:39][CH3:40])=[C:25]([S:27]([C:30]2[CH:31]=[C:32]([C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH2:11])=[CH:4][C:3]=3[CH3:12])[CH:33]=[CH:34][CH:35]=2)(=[O:29])=[O:28])[CH:26]=1)=[NH:21])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 218864724-Bromo-3-methyl-5-nitroanilineHCID 140043492[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]boronic acid

Product 1

HCID 145857684tert-butyl N-[4-[3-(4-amino-2-methyl-6-nitrophenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

Following the procedure used for Example 295, step h, reaction of 4-bromo-3-methyl-5-nitro-phenylamine (350 mg, 1.5 mmol, as prepared in Example 135, step a), {[4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (1.0 gm, 2.27 mmol, as prepared in Example 140, step a), tetrakis(triphenylphosine)palladium(0) (433 mg, 0.375 mmol, Strem Chemicals Inc, Newburyport, Mass.), Na2CO3 (6 mL, 2M), and toluene/EtOH mixture (2:1, 18 mL) at 80° C. for 24 h afforded 250 mg (30%) after purification (SiO2, flash elution: 5% to 50% EtOAc in hexanes) of the title compound as a yellow solid. ESI-MS (m/z): Calcd. for C24H26N4O6S3: 563.1 (M+H); found: 562.8, 463.1 (M−Boc).

Workup

  1. customafforded 250 mg (30%)
  2. customafter purification (SiO2, flash elution: 5% to 50% EtOAc in hexanes) of the title compound as a yellow solid

Sources & evidence

ORD record
ord-f61e02cc43c347b68e864060723871be
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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