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Methanol → 4-(2-Chloro-5-methylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2374136
ノート
印刷プレビュー

反応式

HRID 2374136 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:21])=[O:20])[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)=[O:4].Br[C:32]1[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([Cl:39])[CH:33]=1.CO.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.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][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:20])=[O:21])[CH:7]=[C:8]([C:32]2[C:37]([CH3:38])=[CH:36][N:35]=[C:34]([Cl:39])[CH:33]=2)[CH:9]=1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 534399184-Bromo-2-chloro-5-methylpyridineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 866027194-(2-Chloro-5-methylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester収率 43.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (125 mg, 0.29 mmol, 0.6 equiv.) and 4-bromo-2-chloro-5-methylpyridine (96 mg, 0.47 mmol, 1.0 equiv.) were dissolved in benzene (4 mL). After adding methanol (0.94 mL) and aqueous Na2CO3, Pd(PPh3)4 (108 mg, 0.094 mol, 0.2 equiv.) was then added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2SO4, the solvent was removed under reduced pressure. The crude material was purified by reversed phase HPLC (acetonitrile/water/TFA), yielding the title compound as a colorless solid (54 mg, 0.125 mmol, HPLC Rt 9.087 min, ES+433.0, ES−431.0).

後処理

  1. additionwas then added
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 16 hours
  4. washwashed with water
  5. dry with materialAfter drying the organic layer over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was purified by reversed phase HPLC (acetonitrile/water/TFA)

出典と根拠

ORDレコード
ord-f7afad396acd4b7db3e143fbd08b8443
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07462612B2

反応ノート

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