tert-Butanol → HCID 67353414、化合物

HRID 2405083ノート

反応式

HRID 2405083 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[CH:5]=[CH:4]1)[CH3:2].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>O1CCOCC1.[Cl-].[Na+].O>[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([NH:17][C:20](=[O:29])[O:43][C:39]([CH3:42])([CH3:41])[CH3:40])[N:8]=[CH:7][C:6]=2[CH:5]=[CH:4]1)[CH3:2]

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 673540951H-Pyrrolo[3,2-c]pyridine-6-carboxylic acid, 1-ethyl-

生成物 1

HCID 67353414HCID 67353414、化合物収率 45%

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

In a 500 mL pear flask was added 1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1G, assumed 30.4 mmol) in dioxane (90 ml) and t-butanol (90 ml) to give a brown suspension. To this was then added triethylamine (5.5 ml, 40 mmol) and the mixture was then heated to 85° C. After 7 hours, the reaction did not change much from the 25% conversion achieved in the first two hours. An additional 4.3 ml of diphenylphosphoryl azide (0.65 eq.) was added the next morning and after 5 hours, the reaction has progressed significantly. Brine was added and the mixture was extracted twice with ethyl acetate. Combined organic layers were dried over MgSO4, filtered and concentrated. Crude product was purified by column chromatography (SiO2, eluting with a gradient of 20-30% EtOAc/hexanes) to give tert-butyl 1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1H, 3.6 g, 45%).

後処理

  1. customto give a brown suspension
  2. customachieved in the first two hours
  3. waitafter 5 hours
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. dry with materialCombined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrude product was purified by column chromatography (SiO2
  9. washeluting with a gradient of 20-30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-486e66655c9445b3a1458f0136edbad0
出典データセット
uspto-grants-2014_08
特許番号
US08802695B2

反応ノート

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