1,8-Diazabicyclo(5.4.0)undec-7-ene → phenylphosphonic acid 1-acetyl-1H-indazol-5-yl ester 4-nitrophenyl ester

HRID 1726093Notes

Reaction equation

HRID 1726093 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][P:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=O)[O:12]C2C=CC([N+]([O-])=O)=CC=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:39](=[O:41])[CH3:40])[N:34]=[CH:33]2.N12CCCN=C1CCCCC2>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][P:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:12])[O:29][C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[N:35]([C:39](=[O:41])[CH3:40])[N:34]=[CH:33]3)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 170133Bis(4-nitrophenyl) P-phenylphosphonateHCID 225670481-(5-hydroxy-1H-indazol-1-yl)-Ethanone

Product 1

HCID 57562494phenylphosphonic acid 1-acetyl-1H-indazol-5-yl ester 4-nitrophenyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.36 g of phenylphosphonic acid bis-(4-nitrophenyl) ester (prepared according to procedure E) in 60 ml of dichloromethane is cooled in an ice bath. 1.041 g of 1-(5-hydroxyindazol-1-yl)ethanone and 900 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene in 40 ml of dichloromethane are added thereto and the reaction is continued at 20° C. for 2 hours. The reaction medium is washed with a saturated sodium bicarbonate solution until discoloration of the organic phase. After separation by settling out, the organic extracts are dried over magnesium sulfate and then evaporated under reduced pressure. 2.4 g of phenylphosphonic acid 1-acetyl-1H-indazol-5-yl ester 4-nitrophenyl ester are isolated, which compound is used without purification in the subsequent stage.

Workup

  1. washThe reaction medium is washed with a saturated sodium bicarbonate solution until discoloration of the organic phase
  2. customAfter separation
  3. dry with materialthe organic extracts are dried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-af7392742c9e4092b35bee02d8747a6b
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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