3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal → 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-ol

HRID 218179Notes

Reaction equation

HRID 218179 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:29][Mg]Br>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:18]([CH3:22])([CH3:21])[CH:19]([OH:20])[CH3:29])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 592510413-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanalHCID 178418573HCID 178418573, compound

Product 1

HCID 592510984-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-olYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal (from Ex 116(b), 25 mg, 0.067 mmol) in THF (1 ml) at 0° C. was added a solution of 1.4 M methylmagnesium bromide in 1 ml of THF (1.4 M) dropwise. After 1 hr, the reaction was quenched with sat. NH4Cl and was extracted with ethyl acetate. The organic phase was washed, dried over MgSO4, filtered, and concentrated to give 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-ol as a white solid (24 mg, 92% yield). It is a mixture of diastereomers in a 1:1 ratio. 1H NMR (400 MHz, MeOD) δ ppm 8.20 (1 H, d, J=5.09 Hz) 7.96 (1 H, d, J=9.16 Hz) 7.68-7.75 (2 H, m) 7.59-7.67 (2 H, m) 7.53 (2 H, dd, J=7.63, 2.54 Hz) 7.23-7.35 (4 H, m) 7.14-7.20 (1 H, m) 4.40 (1 H, s) 3.50-3.60 (1 H, m) 1.10 (3 H, 2 singlets,) 1.05 (3 H, s) 0.99 (3 H, 2 singlets). LC/MS (m/z) 389.3 [(M+1)+]; HPLC Rt: 3.96 min.

Workup

  1. customthe reaction was quenched with sat. NH4Cl
  2. extractionwas extracted with ethyl acetate
  3. washThe organic phase was washed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-635a08b4f1e74726bdc4b83816341247
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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