Sodium Carbonate → tert-Butyl 2-(3-cyanophenyl)-3-(2'-methylthiobiphenyl-4-ylaminocarbonyl)-3-propylcarbazate

HRID 22641Notes

Reaction equation

HRID 22641 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].[CH3:31][S:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O.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: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]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[S:32][CH3:31])=[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]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 11191609tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate

Product 1

HCID 22591496tert-Butyl 2-(3-cyanophenyl)-3-(2'-methylthiobiphenyl-4-ylaminocarbonyl)-3-propylcarbazateYield 85.9%

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 0.968 g (5.766 mmol) of 2-(methylthio)-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 atmosphere for 3 h. After customary work-up, 1.28 g (75.9%) of 409 are thus obtained as crystals having a melting point of 184-185° C.; MS(FAB)=517.

Sources & evidence

ORD record
ord-2afadabeeba04b919f5703d1f49b9196
Source dataset
uspto-grants-2005_02
Patent number
US06849626B2

Reaction notes

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