Tetrahydrofuran → 3-(6-Cyano-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

HRID 2215773노트

반응식

HRID 2215773 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([NH2:14])=[O:13])[CH:4]=[CH:3]1.C[O:16][C:17](=O)[C:18]([C:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]#[N:30])=[CH:26][CH:27]=2)[NH:22][CH:21]=1)=O.CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[C:29]([C:25]1[CH:24]=[C:23]2[C:28]([C:20]([C:18]3[C:17](=[O:16])[NH:14][C:12](=[O:13])[C:11]=3[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[N:2]([CH3:1])[CH:3]=[CH:4]4)=[CH:21][NH:22]2)=[CH:27][CH:26]=1)#[N:30]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 114353972-(1-methyl-1H-indol-7-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 69642384(6-cyano-1H-indol-3-yl)-oxo-acetic acid methyl ester

생성물 1

HCID 219500243-(6-Cyano-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-(1-methyl-1H-indol-7-yl)-acetamide (0.410 g, 2.18 mmol) and (6-cyano-1H-indol-3-yl)-oxo-acetic acid methyl ester (0.480 g, 2.10 mmol) in DMF (30 mL) under N2 was added a 1.0 M solution of potassium-tert-butoxide in THF (7.6 mL, 7.6 mmol) dropwise over 5 minutes. The mixture was heated at 70° C. for 17 h. The mixture was cooled to room temperature, quenched with 1N HCl (excess) and poured into EtOAc. The organic layer was separated, washed with water (3×), saturated aq NaHCO3, and brine, dried (MgSO4), filtered and concentrated onto flash SiO2. Flash chromatography (60–70% EtOAc/hex) gave the title compound as a bright orange-red solid which was dried under vacuum at 75° C. overnight (0.416 g, 54%). 1H NMR (400 MHz, DMSO-d6) 12.29 (br s, 1H), 11.26 (s, 1H), 8.03 (d, J=2.3 Hz, 1H), 7.86 (br s, 1H), 7.63 (d, J=8 Hz, 1H), 7.25 (d, J=3 Hz, 1H), 6.99 (dd, J=8, 8 Hz, 1H), 6.91 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 6.60 (d, J=8 Hz, 1H), 6.49 (d, J=3 Hz, 1H), 3.66 (s, 3H). IR (KBR, cm−1) 3282, 2223, 1751, 1698. MS (electrospray, m/z) 367.1 (M++1), 365.2 (M−−1). HRMS 367.1190 (M++1, calcd for C22H15N4O2 367.1195).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with 1N HCl (excess)
  3. additionpoured into EtOAc
  4. customThe organic layer was separated
  5. washwashed with water (3×), saturated aq NaHCO3, and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated onto flash SiO2

출처 및 근거

ORD 기록
ord-3eede39ea4314d2997e960f1a1b66f39
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109229B2

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