Potassium Carbonate → 1,7-Bis-(1H-indol-5-yl)-isoquinoline

HRID 63246

반응식

HRID 63246 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[NH:13]1[C:21]2[C:16](=[CH:17][C:18](B(O)O)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:9]3[C:10]4[C:5](=[CH:4][CH:3]=[C:2]([C:18]5[CH:17]=[C:16]6[C:21](=[CH:20][CH:19]=5)[NH:13][CH:14]=[CH:15]6)[CH:11]=4)[CH:6]=[CH:7][N:8]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27343615-Indolylboronic acidHCID 65020247-Bromo-1-Chloroisoquinoline

생성물 1

HCID 533794811,7-Bis-(1H-indol-5-yl)-isoquinoline수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 7-bromo-1-chloroisoquinoline (0.20 g, 2.1 mmol), 5-indoleboronic acid (0.80 g, 5.0 mmol), tetrakis(triphenylphosphene)palladium (0.19 g, 0.16 mmol), potassium carbonate (2.1 mL, 2 M, 4.1 mmol), N,N-dimethylformamide (11 mL) was stirred while purging the headspace with argon for 30 min. The mixture was then brought to reflux for 16 h before being allowed to cool to RT. The mixture was filtered through a bed of silica gel, diluted with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated and washed with NaOH (2×20 mL, 10% aq.), water (5×30 mL, until refractive changes were no longer seen at the organic-aqueous interface), and ammonium chloride (20 mL, sat.). The organic layer was then adsorbed onto silica gel and flash-chromatographed (ethyl acetate/hexanes) to afford 0.29 g (39%) of a yellow solid. MS (ESI): calculated for C25H17N3, 359.1. found 360.2 [M+H]+382.1 [M+Na]+, and 358.0 [M−H]−. 1H NMR (500 MHz, DMSO-d6) δ 6.46-6.50 (m, 1H) 6.52-6.59 (m, 1H) 7.34-7.36 (m, 1H) 7.36-7.41 (m, 2H) 7.42-7.52 (m, 3H) 7.58 (d, J=8.30 Hz, 1H) 7.81 (dd, J=5.49, 5.00 Hz, 2H) 7.92 (s, 1H) 8.08-8.17 (m, 2H) 8.33 (s, 1H) 8.54 (d, J=5.61 Hz, 1H) 11.18 (br. s., 1H) 11.30 (br. s., 1H) ppm.

후처리

  1. customwhile purging the headspace with argon for 30 min
  2. temperatureto reflux for 16 h
  3. filtrationThe mixture was filtered through a bed of silica gel
  4. additiondiluted with water (50 mL)
  5. extractionextracted with ethyl acetate (50 mL)
  6. customThe organic layer was separated
  7. washwashed with NaOH (2×20 mL, 10% aq.), water (5×30 mL
  8. customflash-chromatographed (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-7a34b072c8c948a6ab8d97b5dad08086
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447049B2

연결된 노트

불러오는 중…