4-Dimethylamino-1-naphthaldehyde → (4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol

HRID 907512Notes

Reaction equation

HRID 907512 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH2:26][OH:27].I[C:29]1[N:30]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[C:32]([CH3:34])[N:33]=1.C([Mg]Br)C.[CH3:58][N:59]([CH3:72])[C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[C:63]([CH:70]=[O:71])=[CH:62][CH:61]=1>ClCCl.CO>[CH3:31][N:30]([CH3:29])[C:35]1[C:42]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:52]([CH:26]([C:3]2[N:4]=[CH:5][N:6]([C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:2]=2[CH3:1])[OH:27])=[CH:53][CH:48]=1.[CH3:58][N:59]([CH3:72])[C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[C:63]([CH:70]([C:31]2[N:30]([C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:29]=[N:33][C:32]=2[CH3:34])[OH:71])=[CH:62][CH:61]=1

Participants

8

Reactant 4

HCID 6080524-Dimethylamino-1-naphthaldehydeHCID 10411451iodo-4-methyl-1-trityl-1H-imidazoleHCID 11544901(5-Methyl-1-trityl-1H-imidazol-4-yl)methanolHCID 178418443HCID 178418443, compound

Product 2

HCID 67026323(4-(dimethylamino)naphthalen-1-yl)(5-methyl-1-trityl-1H-imidazol-4-yl)methanolHCID 67026330(4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanolYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

(4-Dimethylamino)naphthalen-1-yl)(5-methyl-1-trityl-1H-imidazol-4-yl)methanol and (4-(dimethylamino)naphthalen-1-yl)-4-methyl-1-trityl-1H-imidazol-5-yl)methanol (4): A solution of (2) (5.1 g, 11.3 mmol) in dichloromethane (70 ml) was added ethyl magnesium bromide (3.0 M in diethyl ether, 3.8 mL, 11.4 mmol) drop wise at rt. The mixture was stirred for 1 h and a solution of 4-(dimethylamino)-1-naphthaldehyde (3) (1.15 g, 7.35 mmol) in dichloromethane (30 mL) was added drop wise via addition funnel. The reaction mixture was stirred at room temperature (n) overnight. The reaction mixture was quenched with ammonium chloride (aq). The resulting aqueous layer was extracted twice with dichloromethane (300 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 1 to 2% saturated ammonia methanol in dichloromethane to give a crude (4-(dimethylamino)naphthalen-1-yl)(5-methyl-1-trityl-1H-imidazol-4-yl)methanol and (4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol (4) (3.35 g, 6.40 mmol, 87% yield).

Workup

  1. additionwise via addition funnel
  2. customThe reaction mixture was quenched with ammonium chloride (aq)
  3. extractionThe resulting aqueous layer was extracted twice with dichloromethane (300 mL)
  4. dry with materialThe pooled organic layers were dried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customthe solvents were removed under vacuum
  7. customThe residue was purified by chromatography on silica gel with 1 to 2% saturated ammonia methanol in dichloromethane

Sources & evidence

ORD record
ord-35d00d6e4f724ae586fa2ce64b25fbf8
Source dataset
uspto-grants-2011_09
Patent number
US08013169B2

Reaction notes

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