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

HRID 1726077
ノート
印刷プレビュー

反応式

HRID 1726077 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
105 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ee35ea18e451418c875632cfed42ed03
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07491710B2

反応ノート

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