tert-Butanol → HCID 67357244, 화합물

HRID 2405091노트

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HRID 2405091 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.CC[N:20]([CH2:23]C)CC.[Br:25][C:26]1[C:30]2[CH:31]=[N:32][C:33](C(O)=O)=[CH:34][C:29]=2[N:28]([CH2:38][CH3:39])[CH:27]=1.[CH3:40][C:41]([OH:44])([CH3:43])[CH3:42]>CN(C=O)C>[Br:25][C:26]1[C:30]2[CH:31]=[N:32][C:33]([NH:20][C:23](=[O:8])[O:44][C:41]([CH3:43])([CH3:42])[CH3:40])=[CH:34][C:29]=2[N:28]([CH2:38][CH3:39])[CH:27]=1

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 71087282HCID 71087282, 화합물

생성물 1

HCID 67357244HCID 67357244, 화합물수율 9.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A mixture of diphenylphosphoryl azide (4.3 g, 16 mmol), Et3N (7.3 ml, 52 mmol) and 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3B, 2.8 g, 10 mmol) in DMF (30 ml) was stirred at 0° C. for 1 h. The mixture was extracted with EtOAc/H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was dissolved in toluene (30 ml) and added 2-methylpropan-2-ol (3.9 g, 52 mmol). The mixture was stirred at 70° C. for 2 h. The mixture was concentrated in vacuo and purified by chromatography (SiO2, hexanes:EtOAc=1:1) to give tert-butyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (3C, 340 mg, 0.99 mmol, 9.5% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (t, J=7.20 Hz, 3H) 1.49 (s, 9H) 4.14 (q, J=7.33 Hz, 2H) 7.60 (s, 1H) 7.83 (d, J=0.76 Hz, 1H) 8.36 (d, J=0.76 Hz, 1H) 9.59 (s, 1H).

후처리

  1. extractionThe mixture was extracted with EtOAc/H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude mixture was dissolved in toluene (30 ml)
  6. stirringThe mixture was stirred at 70° C. for 2 h
  7. concentrationThe mixture was concentrated in vacuo
  8. custompurified by chromatography (SiO2, hexanes:EtOAc=1:1)

출처 및 근거

ORD 기록
ord-a719868312ca4b47b686ffc22d1a0a7c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802695B2

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