Water → HCID 68883677, compound

HRID 1295057Notes

Reaction equation

HRID 1295057 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](Cl)(=[O:33])[CH2:31][CH3:32].O>C(Cl)Cl>[C:30]([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:33])[CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 135407148680611-44-3

Product 1

HCID 68883677HCID 68883677, compoundYield 88.3%

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 propionyl chloride (0.035 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 (0.106 g, 88%).

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-20e6f240de0f480a8e6e449222a0989f
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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