tert-Butanol → {6-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1-trityl-1H-indazol-5-yl}carbamic Acid Tert-Butyl Ester

HRID 34018Notes

Reaction equation

HRID 34018 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](/[CH:30]=[CH:31]/[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=3)=[N:7][N:8]2[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1C(O)=O.C([N:44]([CH2:47]C)CC)C.[CH3:49][C:50]([OH:53])([CH3:52])[CH3:51].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:61])C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:50]([O:53][C:47](=[O:61])[NH:44][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[F:1])[N:8]([C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:7]=[C:6]2/[CH:30]=[CH:31]/[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=1)([CH3:52])([CH3:51])[CH3:49]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 689303146-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1-trityl-1H-indazole-5-carboxylic Acid

Product 1

HCID 68932770{6-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1-trityl-1H-indazol-5-yl}carbamic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 369 mg of 6-fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1-trityl-1H-indazole-5-carboxylic acid obtained by Production example 108 in 6 mL of toluene were added 69 mg of triethylamine, 0.15 mL of 2-methyl-2-propanol and 187 mg of diphenyl phosphoryl azide, and stirred at 80° C. for 7.5 hours. After adding 10 mL of ethyl acetate to the reaction solution, the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product purified and separated by silica gel column chromatography (n-hexane:toluene=1:1), to afford 102 mg of the title compound as a white non-crystalline powder.

Workup

  1. washthe organic layer was washed successively with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product purified
  5. customseparated by silica gel column chromatography (n-hexane:toluene=1:1)

Sources & evidence

ORD record
ord-331933e3aa3944b0aa0f0112d4f29c1a
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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