Sodium hydride → Ethyl 6-[N-(2-benzyloxy-5-bromobenzyl)-N-(tert-butoxycarbonyl)amino]-3-pyridazinecarboxylate

HRID 1455989Notes

Reaction equation

HRID 1455989 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[N:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=1[CH2:35]Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H-].[Na+]>CN(C=O)C.C(OCC)C>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=1[CH2:35][N:8]([C:9]1[N:14]=[N:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzeneHCID 22105617Ethyl 6-(tert-butoxycarbonylamino)-3-pyridazine carboxylate

Product 1

HCID 22105523Ethyl 6-[N-(2-benzyloxy-5-bromobenzyl)-N-(tert-butoxycarbonyl)amino]-3-pyridazinecarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 6-(tert-butoxycarbonylamino)-3-pyridazine carboxylate (2.4 g), 1-(benzyloxy)-2-bromomethyl-4-bromobenzene (3.2 g) and sodium hydride (0.5 g of a 50% W/W dispersion in oil) in DMF was stirred for 2 hours. The mixture was diluted with diethyl ether and washed with water. The organic solution was dried (MgSO4), filtered and evaporated. Ethyl 6-[N-(2-benzyloxy-5-bromobenzyl)-N-(tert-butoxycarbonyl)amino]-3-pyridazinecarboxylate was isolated by flash chromatography, eluting with 2% ethyl acetate in CH2Cl2. Yield: 1.7 g.

Workup

  1. washwashed with water
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a147f11987cf49a8969347a948eb2d13
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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