Dimethylformamide → 1-Benzyl-7-benzyloxy-3-formyl-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734521Notes

Reaction equation

HRID 1734521 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10](Br)=[C:9]1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:34]=[O:35]>CCCCCC.O1CCCC1>[CH2:1]([N:8]1[C:12]2=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([CH:34]=[O:35])=[C:9]1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 194377641-Benzyl-7-benzyloxy-3-bromo-2-methylpyrrolo[2,3-d]pyridazineHCID 178418339Butyllithium

Product 1

HCID 194377541-Benzyl-7-benzyloxy-3-formyl-2-methylpyrrolo[2,3-d]pyridazineYield 32%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

5.0 g (12.2 mmol) of 1-benzyl-7-benzyloxy-3-bromo-2-methylpyrrolo[2,3-d]pyridazine, 9 ml (14.7 mmol) of a 15% strength solution of n-butyllithium in hexane and 2.4 ml (29.4 mmol) of dimethylformamide are reacted in 125 ml of anhydrous tetrahydrofuran as described for Example 2a. Yield: 32%, m.p.: 147°-149° C.

Sources & evidence

ORD record
ord-b311959ca3774da79a2e13d262136ed4
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

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