Methyl iodide → (S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(1-methoxyethyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

HRID 2422564Notes

Reaction equation

HRID 2422564 reaction equation
[F:1][C:2]([F:34])([F:33])[C@:3]([C:7]1[N:8]=[N:9][N:10]([CH2:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:18][C:19]([CH:23]([OH:25])[CH3:24])=[N:20]3)=[CH:15][CH:14]=2)[CH:11]=1)([OH:6])[CH2:4][CH3:5].I[CH3:36].[H-].[Na+]>C1COCC1>[F:34][C:2]([F:1])([F:33])[C@:3]([C:7]1[N:8]=[N:9][N:10]([CH2:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)=[CH:18][C:19]([CH:23]([O:25][CH3:36])[CH3:24])=[N:20]3)=[CH:15][CH:14]=2)[CH:11]=1)([OH:6])[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66791197(S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(1-hydroxyethyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

Product 1

HCID 66790303(S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(1-methoxyethyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(1-hydroxyethyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol (33 mg, 0.070 mmol) in THF (1 mL) was added iodomethane (5 μL, 0.077 mmol) and sodium hydride 60% in oil (6 mg, 0.15 mmol). After 2 h at rt, the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with acetone/dichloromethane, 2:8) gave the title compound. MS (+ESI): 490 (M+H)+.

Workup

  1. customthe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel (eluting with acetone/dichloromethane, 2:8)

Sources & evidence

ORD record
ord-01fa4fa2ca4a4d87adfea873f38ebac6
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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