3,3-Dimethylbutanoyl chloride → HCID 68883430, compound

HRID 1295040Notes

Reaction equation

HRID 1295040 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([F:21])[CH:15]=1.C(N(C(C)C)CC)(C)C.[CH3:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34](Cl)=[O:35]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34]([O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[C:6]3[C:10](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=3)[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=2)=[CH:15][C:16]=1[F:21])=[O:35]

Participants

6

Reactant 3

HCID 815143,3-Dimethylbutanoyl chlorideHCID 81531DiisopropylethylamineHCID 136367441HCID 136367441, compound

Product 1

HCID 68883430HCID 68883430, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(7-chloro-1-propyl-1H-indazole-3-yl)-2-fluorophenol (0.10 g, 0.33 mmol) in dichloromethane (20 mL) at −78° C. was added diisopropylethylamine (0.70 mL, 0.41 mmol), 3,3-dimethylbutanoyl chloride (0.05 mL, 0.35 mmol) and catalytic amount of 4-(dimethylamino)pyridine. The reaction was stirred at this temperature for 30 minutes. The mixture was diluted with dichloromethane and the organic layer washed with 1n hydrochloric acid solution, water and saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the organic phase was filtered and the filtrate evaporated in vacuo to yield crude title compound. The oil was purified by silica gel column chromatography eluting with hexane/ethyl acetate (5/1) to provide the title compound as a white solid (0.11 g, 0.27 mmol, 83%).

Workup

  1. washthe organic layer washed with 1n hydrochloric acid solution, water and saturated aqueous sodium chloride solution
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationthe organic phase was filtered
  4. customthe filtrate evaporated in vacuo
  5. customto yield crude title compound
  6. customThe oil was purified by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-112dd375f3d64c70872ec905246b0d60
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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