Sodium Carbonate → 5-(2-Thiophen-3-yl-phenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 923278노트

반응식

HRID 923278 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][C:19](B(O)O)=[CH:18]1.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][C:19]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH2:11][CH2:10][CH2:9]2)=[CH:18]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 588271225-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

생성물 1

HCID 588271325-(2-Thiophen-3-yl-phenyl)-5,6,7,8-tetrahydroimidazo[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,-tetrahydroimidazo[1,5-a]pyridine (95 mg, 0.343 mmol) in DME (2 mL) is added thiophene-3-boronic acid (53 mg, 0.414 mmol), aqueous Na2CO3 (2M, 0.5 mL, 1.0 mmol), and Pd(PPh3)4 (20 mg). The reaction mixture is run under microwave irradiation at 120° C. for 20 min. The mixture is partitioned between EtOAc and brine. The organic layer is washed by brine, dried over Na2SO4 and concentrated to give an oil. The crude reaction mixture is subjected to flash chromatography eluting with acetone:hexane to yield the desired compound. MS (ESI) m/z 280 (M+H).

후처리

  1. customThe reaction mixture is run under microwave irradiation at 120° C. for 20 min
  2. customThe mixture is partitioned between EtOAc and brine
  3. washThe organic layer is washed by brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude reaction mixture
  8. washeluting with acetone

출처 및 근거

ORD 기록
ord-74c24209bdcc4c10a0d74b38942a4429
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278969B2

반응 노트

불러오는 중…