Réaction #50917

ord-b43242805e624d7fadd674e498ef0b5e

Équation de réaction

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
Rendement 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
Rendement 75.6%

Réactifs

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

Réactifs

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

Solvants

COCCOC
ethylene glycol dimethyl ether

Conditions de réaction

Température
110°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06849626B2uspto-grants-2005_02