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Potassium Carbonate → [3-Acetyl-6-(4-methoxy-benzylamino)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid tert-butyl ester

HRID 1527261
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반응식

HRID 1527261 반응식
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:10][O:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][NH:17][C:18]2[N:23]=[C:22]3[NH:24][CH:25]=[C:26]([C:27](=[O:29])[CH3:28])[C:21]3=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N.C1COCC1>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:24]1[C:22]2=[N:23][C:18]([NH:17][CH2:16][C:15]3[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:31][CH:30]=3)=[CH:19][CH:20]=[C:21]2[C:26]([C:27](=[O:29])[CH3:28])=[CH:25]1)([CH3:9])([CH3:8])[CH3:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium Carbonate2회HCID 79177tert-Butyl bromoacetate2회HCID 682841881-[6-(4-Methoxy-benzylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone

생성물 1

HCID 68283638[3-Acetyl-6-(4-methoxy-benzylamino)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid tert-butyl ester

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 8028Tetrahydrofuran용매

실험 절차

Tert-butyl bromoacetate (27 μL, 0.18 mmol) was added to a suspension of 1-[6-(4-methoxy-benzylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone (0.17 mmol) and potassium carbonate (27.5 mg, 0.20 mmol) in CH3CN (0.33 mL) and THF (0.33 mL). The reaction mixture was stirred at RT for 7 h. Potassium carbonate (27.5 mg, 0.20 mmol) and tert-butyl bromoacetate (27 μL, 0.18 mmol) were added again and stirring was continued overnight, this operation was repeated the next day. The suspension was filtered, the filtrate concentrated under reduced pressure and the crude residue was purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 98:2). TLC, Rf (CH2Cl2/MeOH 9:1)=0.9; MS (UPLC/MS): 410.2 [M+H]+, 819.4 [2M+H]+, 841.3 [2M+Na]+, 454.1 [M+HCOO]−; tR (HPLC conditions f): 2.30 min.

후처리

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customthe crude residue was purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 98:2)
  6. custom2.30 min.

출처 및 근거

ORD 기록
ord-82a0d3638cd741bcafdb3cdb2f2dae95
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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