Water → HCID 22105541, compound

HRID 1455952Notes

Reaction equation

HRID 1455952 reaction equation
[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:10]=1[CH2:11][NH:12][C:13]1[N:18]=[N:17][C:16]([C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:41](Br)[CH:42]=[CH2:43].O>C1COCC1>[CH2:43]([N:12]([C:13]1[N:18]=[N:17][C:16]([C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])=[CH:15][CH:14]=1)[CH2:11][C:10]1[CH:26]=[C:27]([Br:30])[CH:28]=[CH:29][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:42]=[CH2:41]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22105512HCID 22105512, compound

Product 1

HCID 22105541HCID 22105541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of butyl 6-[N-(2-benzyloxy-5-bromobenzyl)amino]pyridazine-3-carboxylate (CF3CO2H salt) (1.2 g) in THF (100 ml) under argon, was added potassium di-(trimethylsilyl)amide [7.0 ml of 0.67M solution in toluene] to give a yellow solution. To the solution was added allyl bromide (0.5 ml). The mixture was stirred for 2 hours, poured into water and extracted with diethyl ether. The organic solution was dried (MgSO4), evaporated and the residue purified by HPLC, eluting with dichloromethane, to give butyl 6-[N-allyl-N-(2-benzyloxy-5-bromobenzyl)amino]pyridazine-3-carboxylate (460 mg) as a gum.

Workup

  1. customto give a yellow solution
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated
  5. customthe residue purified by HPLC
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-e4de51daf136405e86ae56dd89964bed
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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