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Lithium Chloride → (S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone

HRID 2422561
Notes
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Reaction equation

HRID 2422561 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.C([Sn](CCCC)(CCCC)[C:38]([O:40]CC)=[CH2:39])CCC.[Cl-].[Li+].C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:9]3[C:4](=[CH:5][C:6]([CH2:19][N:20]4[CH:24]=[C:23]([C@:25]([OH:32])([C:26]([F:29])([F:28])[F:27])[CH2:30][CH3:31])[N:22]=[N:21]4)=[CH:7][CH:8]=3)[N:3]=[C:2]([C:38](=[O:40])[CH3:39])[CH:11]=2)=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 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 66790923(S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture 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 (235 mg, 0.51 mmol), tributyl(1-ethoxyvinyl)tin (188 μL, 0.56 mmol), tetrakis(triphenylphosphine)palladium (30 mg, 0.025 mmol) and lithium chloride (64 mg, 1.5 mmol) was refluxed in dioxane (10 mL) overnight. An aqueous saturated solution of NaHCO3 was added and the mixture extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduce pressure. THF (5 mL) and 3M HCl (2 mL) were added, and the solution was stirred at rt for 4 h. An aqueous saturated solution of NaHCO3 was added and the mixture 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, 2:8) gave the title compound. MS (+ESI): 473 (M+H)+.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. additionTHF (5 mL) and 3M HCl (2 mL) were added
  6. additionAn aqueous saturated solution of NaHCO3 was added
  7. extractionthe mixture extracted with EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification on silica gel (eluting with ethyl acetate/hexanes, 2:8)

Sources & evidence

ORD record
ord-376859a370dd48e7aeb1c0e59be5833e
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960409B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes