Tetrabutylammonium Fluoride → 2-methyl-6-morpholino-1-(naphthalen-1-ylmethyl)-1H-benzo[d]imidazol-4-ol

HRID 1749565Notes

Reaction equation

HRID 1749565 reaction equation
CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][C:7]1[C:15]2[N:14]=[C:13]([CH3:16])[N:12]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[C:11]=2[CH:10]=[C:9]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:8]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:16][C:13]1[N:12]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[C:11]2[CH:10]=[C:9]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:8]=[C:7]([OH:6])[C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 669769104-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole

Product 1

HCID 669762582-methyl-6-morpholino-1-(naphthalen-1-ylmethyl)-1H-benzo[d]imidazol-4-olYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole in THF (50 mL) was added TBAF (0.64 mL, 1 mol/L) at room temperature and the mixture was stirred for 1 h. TLC showed consumption of starting material. The solvent was removed in-vacuo and the residue was purified by silica gel chromatography eluted with MeOH:DCM=1:60 to afford the desired product as a white solid (150 mg, 94%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 2.94 (t, 4H, J=4.8 Hz), 3.65 (t, 4H, J=4.8 Hz), 5.87 (s, 2H), 6.30 (d, 1H, J=1.8 Hz), 6.35 (d, 1H, J=1.8 Hz), 6.39 (d, 1H, J=7.5 Hz), 7.35 (t, 1H, J=7.5 Hz), 7.60-7.71 (m, 2H), 7.86 (d, 1H, J=8.4 Hz), 8.01 (d, 1H, J=7.5 Hz), 8.23 (d, 1H, J=8.4 Hz); LC-MS: m/e=374[M+1]+

Workup

  1. customconsumption of starting material
  2. customThe solvent was removed in-vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluted with MeOH

Sources & evidence

ORD record
ord-3181f89a620248d09ea67a9dd9577ae6
Source dataset
uspto-grants-2015_10
Patent number
US09156797B2

Reaction notes

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