참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Dimethyl oxalate | HCID 11120 | — |
| 반응물 | 7-(Benzyloxy)-1H-indole | HCID 260798 | — |
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | 1-methyl-1H-indol-7-ol | HCID 22136802 | — |
| 반응물 | Potassium tert-butoxide | HCID 23665647 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 7-Benzyloxy-1-methylindole | HCID 22136813 | — |
반응 단계
1-Methyl-indol-7-ol: A mixture of 7-benzyloxyindole (300 mg, 1.34 mmol), dimethyl oxalate (317 mg, 2.68 mmol) and potassium tert-butoxide (302 mg, 2.68 mmol) in 5 mL DMF was stirred at 110° C. overnight. The solution was poured into NaHCO3 saturated solution (20 mL) and extracted with EtOAc. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed in vacuo to yield 200 mg of 7-benzyloxy-1-methylindole, which was hydrogenated by 5% Pd/C in 20 mL methanol under H2 (50 psi) to yield 90 mg (45.5%) of the title compound. 1H NMR (CDCl3): 7.19–7.16 (m, 1H), 6.94 (d, J=3 Hz, 1H), 6.86 (t, J=7.5 Hz, 1H), 6.48–6.46 (m, 1H), 6.40 (d, J=3 Hz, 1H), 5.05 (s, 1H), 4.07 (s, 3H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07053117B2 |
|---|
| 출처 데이터셋 | uspto-grants-2006_05 |
|---|
| ORD ID | ord-35e34d7e070f47b8a7d4bdd0f163d079 |
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| 출처 메모 | uspto-grants-2006_05 |
|---|
