Diethyl Ether → HCID 59251120, compound

HRID 218133Notes

Reaction equation

HRID 218133 reaction equation
[CH3:1][C:2]([CH3:22])([C@H:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#[N:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:31][CH2:32][CH3:33])C.[F:34][C:35]([F:42])([F:41])CS(Cl)(=O)=O>C1COCC1>[CH3:1][C:2]([CH3:22])([C@H:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][NH:4][C:32](=[O:31])[CH2:33][C:35]([F:42])([F:41])[F:34]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 68706179HCID 68706179, compound

Product 1

HCID 59251120HCID 59251120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(a)(b) To a stirred solution of (S)-2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropanenitrile (40 mg, 0.138 mmol) in anhydrous THF (10 mL) was added 1.0M lithium aluminum hydride in diethyl ether (0.5 mL, 0.5 mmol) portionwise at RT under nitrogen. After stirring at RT for 3 hr, the mixture was carefully quenched with MeOH, poured into brine, extracted with ethyl acetate (2×100 mL), dried (MgSO4) and concentrated. The crude product was coupled with 2,2,2-trifluoroethanesulfonyl chloride (26 mg, 0.14 mmol) using General Coupling Method B to give (S)—N-(2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropyl)-3,3,3-trifluoropropanamide. MS found: (M+H)+=426.

Workup

  1. customthe mixture was carefully quenched with MeOH
  2. additionpoured into brine
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c588145bb1094aaeaef3db36ef2dfbcb
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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