Reacción #50917

ord-b43242805e624d7fadd674e498ef0b5e

Ecuación de reacción

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
405
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate
CC(C)(C)NS(=O)(=O)c1ccccc1B(O)O
2-(t-butylamino-sulfonyl)phenylboronic acid
→
CCCN(C(=O)Nc1ccc(-c2ccccc2S(=O)(=O)NC(C)(C)C)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
406
Rendimiento 75.6%
CCCN(C(=O)Nc1ccc(-c2ccccc2S(=O)(=O)NC(C)(C)C)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
4′-[3-tert-Butoxycarbonyl-3-(3-cyanophenyl)-2-propylcarbazoylamino]-N-tert-butylbiphenyl-2-sulfonamide
Rendimiento 75.6%

Reactantes

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
405
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate
CC(C)(C)NS(=O)(=O)c1ccccc1B(O)O
2-(t-butylamino-sulfonyl)phenylboronic acid

Reactivos

[Cl][Pd][Cl].[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1
PdCl2(dppf)

Disolventes

COCCOC
ethylene glycol dimethyl ether

Condiciones de reacción

Temperatura
110°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

1.5 g (2.883 mmol) of 405 and 1.112 g (4.324 mmol) of 2-(t-butylamino-sulfonyl)phenylboronic acid are dissolved in 100 ml of ethylene glycol dimethyl ether, treated with 63 mg (0.086 mmol) of PdCl2(dppf) and 20.0 ml of 2N sodium carbonate solution and then stirred at 110° C. under a nitrogen atomsphere for 3 h. After customary work-up, 1.32 g (75.6%) of 406 are thus obtained as crystals having a melting point of 173-174° C.; MS(FAB)=606.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06849626B2uspto-grants-2005_02