tert-Butanol → HCID 71087194, 화합물

HRID 2405085노트

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HRID 2405085 반응식
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9](C(O)=O)[N:8]=[CH:7][C:6]=2[C:5]([CH3:15])=[CH:4]1)[CH3:2].C1(P([N:30]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:33][C:34]([OH:37])([CH3:36])[CH3:35].C1[CH2:42][O:41]CC1>>[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([NH:30][C:42](=[O:41])[O:37][C:34]([CH3:36])([CH3:35])[CH3:33])[N:8]=[CH:7][C:6]=2[C:5]([CH3:15])=[CH:4]1)[CH3:2]

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8028Tetrahydrofuran2회HCID 199401P,P-Diphenylphosphinic azideHCID 71087699HCID 71087699, 화합물

생성물 1

HCID 71087194HCID 71087194, 화합물수율 38%

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온도
85 °C

실험 절차

In a 50 ml sealed cap glass vessel, 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1O, 1.75 g, 8.57 mmol), Diphenylphosphoryl azide (2.408 ml, 11.14 mmol), and TEA (2.389 ml, 17.14 mmol) were dissolved in THF (Ratio: 1.000, Volume: 6.00 ml) and added t-BuOH (Ratio: 1.000, Volume: 6 ml) and sealed the cap and heated on oil bath at 85° C. for 2 hrs. Then transferred into round bottom flask using THF, evaporated the reaction mixture and purified using column chromatography (Hexane-Ethyl acetate mixtures). Pure product fractions were collected and concentrated to obtain the product tert-butyl 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1P, 0.9 g, 38% yield) as a fluffy white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.20 Hz, 3H) 1.49 (s, 9H) 2.26 (d, J=1.26 Hz, 3H) 4.06 (q, J=7.24 Hz, 2H) 7.10 (d, J=1.01 Hz, 1H) 7.73 (s, 1H) 8.33-8.51 (m, 1H) 9.49 (br. s., 1H).

후처리

  1. customIn a 50 ml sealed
  2. customcap glass vessel
  3. customsealed the
  4. customcap
  5. customThen transferred into round bottom flask
  6. customevaporated the reaction mixture
  7. custompurified
  8. customPure product fractions were collected
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-539fa6b2acac4e339eac2b025e55fae7
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802695B2

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