Diisobutylaluminumhydride → 1-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carbaldehyde

HRID 2368492Notes

Reaction equation

HRID 2368492 reaction equation
FC1C=CC(N2C(C=O)=CN=C2S)=CC=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]([C:28](N(OC)C)=[O:29])=[CH:26][N:25]=[C:24]2[S:34][CH2:35][C:36]2[C:41]([F:42])=[CH:40][CH:39]=[C:38]([F:43])[C:37]=2[F:44])=[CH:19][CH:18]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]([CH:28]=[O:29])=[CH:26][N:25]=[C:24]2[S:34][CH2:35][C:36]2[C:41]([F:42])=[CH:40][CH:39]=[C:38]([F:43])[C:37]=2[F:44])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 21225700DiisobutylaluminumhydrideHCID 866775411-(4-Fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamideHCID 178519842HCID 178519842, compound

Product 1

HCID 866775501-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carbaldehyde (32) was prepared in a similar manner as that described for the synthesis of compound 12 using 1-(4-fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (9) (1.15 g, 2.7 mmol), diisobutyl aluminum hydride (DiBAL) (1M in THF, 5.5 mL, 5.5 mmol), and THF (5 mL).

Sources & evidence

ORD record
ord-df16d8664b4e4316a70296a325a119d4
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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