Ethanol → tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216005Notes

Reaction equation

HRID 2216005 reaction equation
[CH3:1][C:2]1[C:3](B2OC(C)(C)C(C)(C)O2)=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][C:23](=[O:44])[NH:24][C:25]([C:27]1[S:28][C:29]([S:42][CH3:43])=[C:30]([S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37](Br)[CH:36]=2)(=[O:34])=[O:33])[CH:31]=1)=[NH:26])([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:18]([O:22][C:23](=[O:44])[NH:24][C:25]([C:27]1[S:28][C:29]([S:42][CH3:43])=[C:30]([S:32]([C:35]2[CH:36]=[C:37]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=3[NH2:8])[CH:38]=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH:31]=1)=[NH:26])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 218860963-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)anilineHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The procedure described in Example 1: step c was followed using 3-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (95 mg. 0.41 mmol, Example 25: step b), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (100.7 mg, 0.21 mmol, Example 27: step c), Pd(PPh3)4 (47 mg, 0.04 mmol), aqueous Na2CO3 (2M, 0.8 mL, 1.6 mmol), ethanol (0.8 mL) and toluene (1.6 mL). Purification by preparative SiO2 TLC (33% EtOAc in hexanes) of the residue yielded the title compound (30 mg, 28%) as an off-white solid. ESI-MS (m/z): Calcd. For C24H27N3O4S3: 517.2; found: 517.8.

Workup

  1. customPurification by preparative SiO2 TLC (33% EtOAc in hexanes) of the residue

Sources & evidence

ORD record
ord-3b9bf20bfd124e2180aa0391ac095ba2
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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