tert-Butanol → HCID 67353089、化合物

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.[CH:25]1([CH2:28][N:29]2[C:37]3[CH:36]=[C:35](C(O)=O)[N:34]=[CH:33][C:32]=3[CH:31]=[CH:30]2)[CH2:27][CH2:26]1.[CH3:41][C:42]([OH:45])([CH3:44])[CH3:43]>>[CH:25]1([CH2:28][N:29]2[C:37]3[CH:36]=[C:35]([NH:20][C:23](=[O:8])[O:45][C:42]([CH3:44])([CH3:43])[CH3:41])[N:34]=[CH:33][C:32]=3[CH:31]=[CH:30]2)[CH2:26][CH2:27]1

参加物

反応物 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 67355433HCID 67355433、化合物

生成物 1

HCID 67353089HCID 67353089、化合物収率 26.1%

反応条件

温度: 80 °C

実験手順

A mixture of diphenylphosphoryl azide (1.7 g, 6.2 mmol), Et3N (2.9 ml, 21 mmol) and 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (2B, 0.9 g, 4.0 mmol) in 2-methylpropan-2-ol (10 g, 140 mmol) was stirred at room temperature for 1 h and 80° C. for 3 h. The mixture was extracted with EtOAct/H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was purified by chromatography (SiO2, hexanes:EtOAc=50:50) to give tert-butyl 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (2C, 300 mg, 25% yield) as a white powder. 1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.35-0.44 (m, 2 H) 0.57-0.70 (m, 2 H) 1.19-1.33 (m, 1 H) 1.57 (s, 9 H) 3.97 (d, J=6.82 Hz, 2 H) 6.52-6.54 (m, 1 H) 7.19 (d, J=3.28 Hz, 1 H) 7.59 (br. s., 1 H) 7.93 (s, 1 H) 8.56 (d, J=1.01 Hz, 1 H).