HCID 59331975, compound → {2-(4-Chloro-phenyl)-2-[6-(3-methyl-1-trityl-1H-pyrazol-4-yl)-pyridin-3-yl]-vinyl}-methyl-(1-phenyl-ethyl)-amine

HRID 45531Notes

Reaction equation

HRID 45531 reaction equation
C([Li])CCC.[C:6]1([C:12]([N:21]([CH3:30])[C@@H:22](C2C=CC=CC=2)C)([C:15]2C=CC=CC=2)[PH2]=O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([C:40]2[CH:41]=[N:42][C:43]([C:46]3[C:47]([CH3:70])=[N:48][N:49]([C:51]([C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[CH:50]=3)=[CH:44][CH:45]=2)=O)=[CH:34][CH:33]=1>O1CCCC1>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([C:40]2[CH:41]=[N:42][C:43]([C:46]3[C:47]([CH3:70])=[N:48][N:49]([C:51]([C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[CH:50]=3)=[CH:44][CH:45]=2)=[CH:30][N:21]([CH3:22])[CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:15])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 59331975HCID 59331975, compoundHCID 178418339ButyllithiumHCID 178461684HCID 178461684, compound

Product 1

HCID 76753191{2-(4-Chloro-phenyl)-2-[6-(3-methyl-1-trityl-1H-pyrazol-4-yl)-pyridin-3-yl]-vinyl}-methyl-(1-phenyl-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

n-Butyllithium (0.47 ml, 0.76 mmol, 1.6M in Hexanes) was added dropwise to a solution of (R)(Diphenyl-phosphinoylmethyl)-methyl-(1-phenyl-ethyl)-amine* (0.18 g, 0.51 mmol) in dry tetrahydrofuran (9 ml) at −15° C. After 15 minutes a solution of (4-Chloro-phenyl)-[6-(3-methyl-1-trityl-1H-pyrazol-4-yl)-pyridin-3-yl]-methanone (0.14 g, 0.25 mmol) in tetrahydrofuran (0.9 ml) was added and the reaction mixture was stirred for a further 30 minutes at −15° C. before warming to room temperature over 1 hour. The reaction mixture was quenched with water, extracted with diethyl ether, organic extracts were combined, dried (MgSO4) and concentrated to afford the title compound, which was used in the next step without further purification.

Workup

  1. temperaturebefore warming to room temperature over 1 hour
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with diethyl ether, organic extracts
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1401f71a1cf34abdb7b46f1046ccce95
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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