Hydrochloric Acid → HCID 67249703, 화합물

HRID 1964148

반응식

HRID 1964148 반응식
[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14]CC)=O)=[CH:6]2.[CH3:18][C:19]([O-])(C)C.[K+].C1COCC1.C(OC)(=O)C=C.Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:18][CH2:19][C:12](=[O:14])[C:7]3=[CH:6][C:5]=2[C:4]=1[CH3:17]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 21396313ethyl 5-methoxy-4-methyl-1H-indole-2-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 67249703HCID 67249703, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a suspension of ethyl 5-methoxy-4-methyl-1H-indole-2-carboxylate (712 mg, 3.05 mmol) in toluene (10 mL) was added a 1 M solution of KOtBu in THF (3.97 mL, 3.97 mmol). The reaction mixture was stirred at room temperature for 5 min, methyl acrylate (825 μL, 9.15 mmol) was added. The reaction was stirred at reflux overnight and neutralized with 1 N HCl aqueous solution. The solid was collected and divided into three microwave vial. Each was added AcOH (8 mL) and H2O (1 mL), and heated at 180° C. for 15 min under microwave irradiation. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a yellow solid (500 mg). LCMS m/z=216.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 2.45 (s, 3H), 3.21 (t, J=6.5 Hz, 2H), 3.68 (s, 3H), 4.40 (t, J=6.2 Hz, 2H), 6.98 (s, 1H), 7.13 (d, J=9.0 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H).

후처리

  1. stirringThe reaction was stirred
  2. customThe solid was collected
  3. additionEach was added AcOH (8 mL) and H2O (1 mL)
  4. temperatureheated at 180° C. for 15 min under microwave irradiation
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4b2174b178f749b4a68e483d51cceec3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415484B2

연결된 노트

불러오는 중…