methyl 2-bromo-3-(3-methyl-2-buten-1-yl)-5-formyl-3H-imidazole-4-carboxylate → ethyl 2-bromo-3-(but-2-ynyl)-5-formyl-3H-imidazole-4-carboxylate

HRID 1446044Notes

Reaction equation

HRID 1446044 reaction equation
BrC1N(CC=C(C)C)C(C(OC)=O)=C(C=O)N=1.[Br:18][C:19]1[N:20]([CH2:34][C:35]#[C:36][CH3:37])[C:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:22]([C:24](OCC)=[O:25])[N:23]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[Br:18][C:19]1[N:20]([CH2:34][C:35]#[C:36][CH3:37])[C:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:22]([CH:24]=[O:25])[N:23]=1

Participants

5

Reactant 3

HCID 11580300methyl 2-bromo-3-(3-methyl-2-buten-1-yl)-5-formyl-3H-imidazole-4-carboxylateHCID 21225700DiisobutylaluminumhydrideHCID 59815044diethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 11522264ethyl 2-bromo-3-(but-2-ynyl)-5-formyl-3H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to 1c from 20.00 g (58.28 mmol) diethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate with 70 ml (70 mmol) diisobutylaluminium hydride in 300 ml of tetrahydrofuran.

Sources & evidence

ORD record
ord-1d21c3428e7044608c443188f0b89027
Source dataset
uspto-grants-2010_02
Patent number
US07667035B2

Reaction notes

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