Water → 3-Phenyl-5-(phenylmethoxy)-1H-indazole

HRID 1349586Notes

Reaction equation

HRID 1349586 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C2C=CC=CC=2)=[C:4]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O.C[N:41](C)C=O>>[C:19]1([C:17]2[C:4]3[C:5](=[CH:6][CH:7]=[C:2]([O:1][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:3]=3)[NH:8][N:41]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22480166HCID 22480166, compound

Product 1

HCID 224799253-Phenyl-5-(phenylmethoxy)-1H-indazoleYield 63%

Procedure

To a solution of N-[4-hydroxy-2-(phenylcarbonyl)phenyl]benzamide (4.0 g, 12.6 mmol) in dimethyl formamide (DMF) (15 mL) was added potassium carbonate (K2CO3) (large excess) then benzyl bromide (660 μL, 5.5 mmol). The reaction was stirred overnight. It was added to water (100 mL) then extracted with ethyl acetate (3×40 mL). The combined organic layers were dried (Na2SO4) then concentrated under vacuo to give a solid which was recrystallized with ethyl acetate/hexane to give the title compound (3.24 g, 63% yield, analytical).

Workup

  1. extractionthen extracted with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationthen concentrated under vacuo
  4. customto give a solid which
  5. customwas recrystallized with ethyl acetate/hexane

Sources & evidence

ORD record
ord-02640c61d0944be2b5d12f3c9bf7fe85
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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