tert-Butanol → HCID 67357244、化合物

HRID 2405091ノート

反応式

HRID 2405091 の反応式
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

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 71087282HCID 71087282、化合物

生成物 1

HCID 67357244HCID 67357244、化合物収率 9.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a719868312ca4b47b686ffc22d1a0a7c
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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