Sodium Carbonate → 4'-[3-tert-Butoxycarbonyl-3-(3-cyanophenyl)-2-propylcarbazoylamino]-N-tert-butylbiphenyl-2-sulfonamide

HRID 22639Notes

Reaction equation

HRID 22639 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([N:17]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[O:22])[CH2:18][CH2:19][CH3:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:31]([NH:35][S:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1B(O)O)(=[O:38])=[O:37])([CH3:34])([CH3:33])[CH3:32].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:13]([O:12][C:10]([N:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)[N:17]([CH2:18][CH2:19][CH3:20])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:40]2[C:39]([S:36]([NH:35][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:37])=[O:38])=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:26][CH:25]=1)=[O:22])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 11191609tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate

Product 1

HCID 113424644'-[3-tert-Butoxycarbonyl-3-(3-cyanophenyl)-2-propylcarbazoylamino]-N-tert-butylbiphenyl-2-sulfonamideYield 75.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

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.

Sources & evidence

ORD record
ord-b43242805e624d7fadd674e498ef0b5e
Source dataset
uspto-grants-2005_02
Patent number
US06849626B2

Reaction notes

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