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 1036345노트

반응식

HRID 1036345 반응식
[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]

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 1118Sulfuric Acid용매HCID 6422Trifluoroacetic acid용매HCID 7519Anisole용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-69af30e3d3aa42c883136d548debf54f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546407B2

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