Boron trifluoride etherate → methyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)-2,2-dimethylpropanoate

HRID 563378Notes

Reaction equation

HRID 563378 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](CO)=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.B(F)(F)F.O(CC)[CH2:25]C.[CH3:29][O:30][C:31]([O:35][Si](C)(C)C)=[C:32]([CH3:34])[CH3:33]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:33][C:32]([CH3:25])([CH3:34])[C:31]([O:30][CH3:29])=[O:35])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 67005456(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol

Product 1

HCID 67005217methyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)-2,2-dimethylpropanoateYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-(4-Fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol (178 mg, 0.51 mmol) was dissolved in 5 mL of dry DCM and BF3—OEt2 (0.09 mL, 0.7 mmol) was added portionwise and then stirred 30 min. Then the reaction was treated with 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.43 mL, 2.1 mmol). The reaction was quenched with aqueous sodium bicarbonate and extracted 2×EtOAc, the organic layers dried over MgSO4, filtered, and concentrate. The residue was purified on SiO2 by MPLC using a 5:95 to 1:9 gradient to give 121 mg (51% yield) of methyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)-2,2-dimethylpropanoate. MS found: (M+H)+=341.

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted 2×EtOAc
  3. dry with materialthe organic layers dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrate
  6. customThe residue was purified on SiO2 by MPLC

Sources & evidence

ORD record
ord-b0fb43d3d03c4de18bb14f2c9e333b70
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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