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Formic Acid → 1H-Pyrrolo(2,3-b)pyridine

HRID 603047
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HRID 603047 반응식
COCCOC[N:7]1[C:11]2=[N:12][CH:13]=[C:14](N3CCOCC3)[CH:15]=[C:10]2[C:9](C2C=CC=CC=2OC)=[CH:8]1.C(O)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C.O.[Cl-].[Na+].O>[NH:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[CH:8]1
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참가 물질

8

반응물 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59699905HCID 59699905, 화합물

생성물 1

HCID 92221H-Pyrrolo(2,3-b)pyridine

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962
Water
용매
2회
HCID 57417360Sodium chloride; water용매

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온도
65 °C

실험 절차

65 mg (0.17 mmol) of 1-(2-methoxy-ethoxymethyl)-3-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine was dissolved in a mixture of 3 ml of ethanol and 2 ml of water. 500 μl of formic acid was added and the mixture heated to 65° C. for 16 h and then irradiated in the microwave to 150° C. for 40 min. The resulting mixture was neutralized by addition of sodium bicarbonate and water and the crude distributed between ethyl acetate and brine. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated to afford 47 mg (0.15 mmol, 94% yield) of 3-(2-methoxy-phenyl)-5-morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine. 1H-NMR (d6-DMSO): δ11.58 (s, 1H), 8.11 (d, J=2.5 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.51 (dd, J=1.4 Hz, 7.3 Hz, 1H), 7.46 (s, 1H), 7.27 (ddd, J=1.5 Hz, 8.8 Hz, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.02 (dd(d), J=1.5 Hz, 7.3 Hz, 1H), 3.82 (s, 3H), 3.77 (m, 4H), 3.07 (m, 4H); MS: m/z 310 [MH+].

후처리

  1. customirradiated in the microwave to 150° C. for 40 min
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated

출처 및 근거

ORD 기록
ord-064b408f6384484b80ed49820ac7c2b1
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906648B2

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