HCID 86595422, compound → HCID 59020090, compound

HRID 971150Notes

Reaction equation

HRID 971150 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:29])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([CH:27]=[O:28])[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:30]([F:33])([F:32])[F:31])=[N:10]2)=[CH:5][CH:4]=1.[Zn](C)[CH3:35]>CCOCC.Cl[Ti](Cl)(Cl)Cl>[OH:28][CH:27]([C:24]1([C:21]2[CH:22]=[CH:23][C:18]([N:15]3[CH2:16][CH2:17][C:12]4[C:11]([C:30]([F:33])([F:31])[F:32])=[N:10][N:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[C:13]=4[C:14]3=[O:29])=[CH:19][CH:20]=2)[CH2:25][CH2:26]1)[CH3:35]

Participants

5

Reactant 2

HCID 86595422HCID 86595422, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 59020090HCID 59020090, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

1-{4-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-phenyl}-cyclopropanecarbaldehyde (93 mg, 0.21 mmol) was stirred in Et2O (2 mL) at −78° C. ZnMe2 (2M in toluene, 0.16 mL, 1.5 eq) was added followed by the addition of TiCl4 (1 M in CH2Cl2, 0.3 mL). The resulting mixture was stirred for 1 h. The reaction was quenched by addition of NH4Cl, extracted with EtOAc, washed with H2O and brine, dried over MgSO4, filter, and concentrated. The residue was purified by silica gel column to yield the pure desired product (62 mg, yield: 64.5%). LC/MS (ESI+) 472.6 (M+H)+, tR=2.44 min (35–95% CH3CN/H2O in a 6-min run).

Workup

  1. customThe reaction was quenched by addition of NH4Cl
  2. extractionextracted with EtOAc
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfilter
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-a57fd1d6c9174c5c8dc6678493f2d84f
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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