tert-Butanol → HCID 71087194、化合物

HRID 1478898ノート

反応式

HRID 1478898 の反応式
[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]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8028Tetrahydrofuran2 回HCID 199401P,P-Diphenylphosphinic azideHCID 71087699HCID 71087699、化合物

生成物 1

HCID 71087194HCID 71087194、化合物収率 38%

反応条件

温度
85 °C

実験手順

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. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.20 Hz, 3 H) 1.49 (s, 9 H) 2.26 (d, J=1.26 Hz, 3 H) 4.06 (q, J=7.24 Hz, 2 H) 7.10 (d, J=1.01 Hz, 1H) 7.73 (s, 1 H) 8.33-8.51 (m, 1 H) 9.49 (br. s., 1 H).

後処理

  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

出典と根拠

ORDレコード
ord-7490286d5a384cf6b495419619860403
出典データセット
uspto-grants-2016_08
特許番号
US09403819B2

反応ノート

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