Tetrahydrofuran → 2-(2-benzyl-3-phenyl-2H-indazol-7-yl)propan-2-ol

HRID 735469Notes

Reaction equation

HRID 735469 reaction equation
CO[C:3]([C:5]1[C:13]2C(=C(C3C=CC=CC=3)N(CC3C=CC=CC=3)N=2)C=CC=1)=O.[CH2:27]([N:34]1[C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:41]2[C:36]([C:37](C(O)=O)=[CH:38][CH:39]=[CH:40]2)=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C[Mg+].[Br-].C1C[O:58]CC1>>[CH2:27]([N:34]1[C:42]([C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:43]2[C:48]([C:47]([C:5]([OH:58])([CH3:3])[CH3:13])=[CH:46][CH:45]=[CH:44]2)=[N:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 67021115HCID 67021115, compoundHCID 67021186HCID 67021186, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 670212542-(2-benzyl-3-phenyl-2H-indazol-7-yl)propan-2-ol

Procedure

Ninety milligrams (90 mg; 0.24 mmol) of 2-benzyl-3-phenyl-2H-indazole-7-carboxylic acid methyl ester, prepared from 2-benzyl-3-phenyl-2H-indazole-7-carboxylic acid (see preparation of Example 518), were dissolved in THF and 0.5 ml of 3M MeMgBr in THF (1.4 mmol) were added. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with aq NH4Cl solution and product was extracted with EtOAc, and then flash column chromatography (SiO2, dichloromethane as an eluant) afforded 2-(2-benzyl-3-phenyl-2H-indazol-7-yl)propan-2-ol in 86% yleld.

Workup

  1. customThe reaction mixture was quenched with aq NH4Cl solution and product
  2. extractionwas extracted with EtOAc

Sources & evidence

ORD record
ord-b4a095413e1a46e3b95fb52880486db8
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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