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

HRID 2422558Notes

Reaction equation

HRID 2422558 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([CH2:19][N:20]3[CH:24]=[C:23]([C@@:25]([OH:32])([CH2:30][CH3:31])[C:26]([F:29])([F:28])[F:27])[N:22]=[N:21]3)=[CH:7][CH:8]=2)[N:3]=1.[CH3:33][S-:34].[Na+]>CN(C=O)C>[F:27][C:26]([F:29])([F:28])[C@:25]([C:23]1[N:22]=[N:21][N:20]([CH2:19][C:6]2[CH:5]=[C:4]3[C:9]([C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[CH:11][C:2]([S:34][CH3:33])=[N:3]3)=[CH:8][CH:7]=2)[CH:24]=1)([OH:32])[CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86621982(S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

Product 1

HCID 66790511(S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(methylthio)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol (85 mg, 0.18 mmol) and sodium thiomethoxide (51 mg, 0.72 mmol) in DMF (3 mL) was stirred at rt for 2 h. 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 ethyl acetate/hexanes, 1:9) gave the title compound. MS (+ESI): 477 (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 ethyl acetate/hexanes, 1:9)

Sources & evidence

ORD record
ord-b69205347bb74045b81de15691c8e84a
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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