Cesium carbonate → Tert-butyl 2-(3-cyanophenyl)-3-propyl-3-(2,2,2-trifluoracetyl)carbazate

HRID 22636Notes

Reaction equation

HRID 22636 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F: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(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:31][CH2:32][CH3:33]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([N:17]([CH2:31][CH2:32][CH3:33])[C:18](=[O:23])[C:19]([F:20])([F:22])[F:21])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 22591504Tert-butyl 2-(3-cyanophenyl)-3-(2,2,2-trifluoroacetyl)carbazate

Product 1

HCID 22591513Tert-butyl 2-(3-cyanophenyl)-3-propyl-3-(2,2,2-trifluoracetyl)carbazateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g (15.19 mmol) of the crude product 402 are treated with 7.42 g (22.77 mmol) of cesium carbonate in 100 ml of DMF under a nitrogen atmosphere. After 30 min, 3.87 ml (22.77 mmol) of 1-iodopropane are slowly added dropwise and the mixture is then stirred at RT for 18 h. After customary work-up, 5.64 g (100%) of 403 are thus obtained as an oil, which is employed directly in stage 4.

Sources & evidence

ORD record
ord-59162576c1e84dd196e6a54b89f40050
Source dataset
uspto-grants-2005_02
Patent number
US06849626B2

Reaction notes

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