HCID 57464094, compound → HCID 57455400, compound

HRID 1623167Notes

Reaction equation

HRID 1623167 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH:21]=[O:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].[CH3:23][Mg]Br>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH:21]([OH:22])[CH3:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 57464094HCID 57464094, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57455400HCID 57455400, compound

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

The general method described in Part G of Example 28 was used to react 4-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (8.5 g, 28.8 mmol) with methylmagnesium bromide (20.6 mL of a 1.4 M solution in toluene/THF, 28.8 mmol) to provide 5-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol (3.54 g) as an off-white solid after chromatography on silica gel (elution with 5% methanol in dichloromethane).

Sources & evidence

ORD record
ord-af1a68368de84dc389835ff5a300f2b8
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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