Cesium carbonate → HCID 57749163, compound

HRID 1874359Notes

Reaction equation

HRID 1874359 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[N:28][CH:29]=1>CN(C)C=O>[CH3:16][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:24]2[CH:29]=[N:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[CH:7][C:6]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 577492931,1-Dimethylethyl N-(5-hydroxy-2-methylphenyl)carbamate

Product 1

HCID 57749163HCID 57749163, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the same manner as in Reference Example 33 and using tert-butyl (5-hydroxy-2-methylphenyl)carbamate (18.9 g, 85.0 mmol), cesium carbonate (41.8 g, 0.128 mol), N,N-dimethylformamide (100 mL) and 5-bromo-2-nitropyridine (16.4 g, 80.7 mmol) as starting materials, the title compound (19.5 g, 53%) was obtained as a pale-yellow oil.

Sources & evidence

ORD record
ord-5fd993cc21094f3fa402df2fc3e000c1
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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