Sodium Carbonate → 5-(2-Thiophen-2-yl-phenyl)-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine

HRID 923277노트

반응식

HRID 923277 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH2:11][CH2:10][CH2:9]1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH2:11][CH2:10][CH2:9]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 588271225-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

생성물 1

HCID 588271095-(2-Thiophen-2-yl-phenyl)-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 5-(2-bromophenyl)-5,6,7,8,-tetrahydro-imidazo[1,5-a]pyridine, Example 12D (120 mg, 0.43 mmol) in DME (2 mL) is added thiophene-2-boronic acid (166 mg, 1.3 mmol), aqueous Na2CO3 (2M, 1.0 mL, 2.0 mmol), and Pd(PPh3)4 (20 mg). The reaction mixture is refluxed overnight. The mixture is partitioned between EtOAc and 1M NaOH. The organic layer is washed by sat. NaHCO3, dried and concentrated to give an oil. The crude reaction mixture is subjected to flash chromatography (silica gel) eluting with acetone:hexane to yield the desired compound. MS (ESI) m/z 280 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.58-1.74 (m, 1H), 1.85-2.01 (m, 2H), 2.14-2.27 (m, 1H), 2.74-2.94 (m, 2H), 5.45 (dd, J=8.6, 5.1 Hz, 1H), 6.81 (s, 1H), 7.00-7.05 (m, 2H), 7.06 (s, 1H), 7.10 (dd, J=5.3, 3.5 Hz, 1H), 7.31-7.37 (m, 2H), 7.39 (dd, J=5.2, 1.1 Hz, 1H), 7.41-7.46 (m, 1H).

후처리

  1. temperatureThe reaction mixture is refluxed overnight
  2. customThe mixture is partitioned between EtOAc and 1M NaOH
  3. washThe organic layer is washed by sat. NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude reaction mixture
  8. washeluting with acetone

출처 및 근거

ORD 기록
ord-165c98b3cbbc48f78ca3bde0beadf560
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278969B2

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