Water → HCID 68883352, compound

HRID 1295056Notes

Reaction equation

HRID 1295056 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])=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C.[C:30]([CH2:34][C:35](Cl)=[O:36])([CH3:33])([CH3:32])[CH3:31].O>C(Cl)Cl>[CH3:31][C:30]([CH3:33])([CH3:32])[CH2:34][C:35]([O:20][C:17]1[CH:16]=[CH:15][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:19][CH:18]=1)=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 815143,3-Dimethylbutanoyl chlorideHCID 81531DiisopropylethylamineHCID 135407148680611-44-3

Product 1

HCID 68883352HCID 68883352, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(7-chloro-1-propyl-1H-indazol-3-yl)phenol (0.100 g, 0.35 mmol) and N,N-diisopropylethyl amine (0.5 g, 0.38 mmol) in CH2Cl2 (5 mL) was added dropwise tert-butylacetyl chloride (0.051 g, 0.38 mmol). The solution was allowed to stir overnight at room temperature. Water was added and the solution was extracted with CH2Cl2. The organic layer was washed with brine and dried (MgSO4). The product was purified by flash chromatography (5/1 hexane/ethyl acetate) to yield a white solid (0.098 g, 72%).

Workup

  1. extractionthe solution was extracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe product was purified by flash chromatography (5/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-76fa98f30a2e451d955ef48eaf43dfb0
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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