4-chloro-1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester → Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 2405999ノート

反応式

HRID 2405999 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[C:8]2[CH:14]=[CH:13][N:12](CC3C=CC(OC)=CC=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O.OS(O)(=O)=O.C1(OC)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

参加物

5

反応物 1

HCID 578991914-chloro-1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester

生成物 1

HCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate収率 46.3%

試薬・触媒・溶媒 3

HCID 1118Sulfuric Acid溶媒HCID 6422Trifluoroacetic acid溶媒HCID 7519Anisole溶媒

実験手順

To a solution of 4-chloro-1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester (prepared as described in J. Heterocycl. Chem. 1972, 235 and Bioorg. Med. Chem. Lett. 2003, 2405) (3.48 g, 10 mmol) in TFA (20 mL), conc. H2SO4 (1.5 mL) and anisole (3 mL) were added at room temperature. The resulting solution was stirred at this temperature for 3 hours and then basified slowly by addition of ice-cold aqueous NaHCO3. The aqueous solution was extracted with ethyl acetate and the combined organic layers were dried (Na2SO4) and concentrated. The residue was filtered and washed with n-hexanes to give a yellow solid (1.04 g, 46%). LC-MS (LCT2) m/z 226 [M+H+], Rt 6.22 min.

後処理

  1. additionbasified slowly by addition of ice-cold aqueous NaHCO3
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. filtrationThe residue was filtered
  6. washwashed with n-hexanes

出典と根拠

ORDレコード
ord-f6e16a32dbbb4848a0d3dca4e9636b78
出典データセット
uspto-grants-2014_08
特許番号
US08809336B2

反応ノート

読み込み中…