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Triethylamine → (1-acetyl-1H-indazol-5-yl)phosphonic Acid Dimethyl Ester

HRID 1726077
Notes
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Reaction equation

HRID 1726077 reaction equation
[CH3:1][O:2][P:3]([O-:6])[O:4][CH3:5].C(N(CC)CC)C.[C:14]([N:17]1[C:25]2[C:20](=[CH:21][C:22](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:24]=2)[CH:19]=[N:18]1)(=[O:16])[CH3:15]>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][P:3]([C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[N:17]([C:14](=[O:16])[CH3:15])[N:18]=[CH:19]2)(=[O:6])[O:4][CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 21884954DimethylphosphiteHCID 57562419trifluoromethanesulfonic acid 1-acetyl-1H-indazol-5-yl ester

Product 1

HCID 57562465(1-acetyl-1H-indazol-5-yl)phosphonic Acid Dimethyl EsterYield 55.2%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

291 μl (1.09 eq; 3.172 mmol) of dimethylphosphite, 442 μl (1.09 eq; 3.172 mmol) of triethylamine and 134 mg (0.04 eq; 0.116 mmol) of tetrakis(triphenylphosphine)palladium(0) are stirred under an argon atmosphere for 15 minutes. 897 mg (1 eq; 2.91 mmol) of trifluoromethanesulfonic acid 1-acetyl-1H-indazol-5-yl ester in solution in 60 ml of dimethylformamide. The medium is heated at 105° C. for 4 hours under an argon atmosphere. The solvent is evaporated off under reduced pressure in a rotary evaporator, with 40 ml of toluene being added. The reaction crude is taken up in 40 ml of ethyl acetate and then washed with 50 ml of water. The organic phase is dried over magnesium sulfate and then filtered and the solvent is evaporated off under reduced pressure in a rotary evaporator. 973.6 mg of crude product are obtained. The reaction crude is purified by flash chromatography (silica 35-70 μm), eluent: ethyl acetate/cyclohexane 80:20 to obtain 430.5 mg of (1-acetyl-1H-indazol-5-yl)phosphonic acid dimethyl ester.

Workup

  1. customThe solvent is evaporated off under reduced pressure in a rotary evaporator, with 40 ml of toluene being
  2. additionadded
  3. customThe reaction crude
  4. washwashed with 50 ml of water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure in a rotary evaporator
  8. custom973.6 mg of crude product are obtained
  9. customThe reaction crude
  10. customis purified by flash chromatography (silica 35-70 μm), eluent

Sources & evidence

ORD record
ord-ee35ea18e451418c875632cfed42ed03
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07491710B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes