Sodium Carbonate → HCID 21716778, 화합물

HRID 1385995노트

반응식

HRID 1385995 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:7]=1.[C:13]([O:17][C:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](B(O)O)=[CH:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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:10]1[CH:11]=[CH:12][C:8]([C:6]2[CH:7]=[C:2]([C:22]3[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH:21]=3)[CH:3]=[N:4][CH:5]=2)=[CH:9]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 52330101-(tert-Butoxycarbonyl)indole-3-boronic acidHCID 112764923-Bromo-5-thiophen-3-yl-pyridine

생성물 1

HCID 21716778HCID 21716778, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A deoxygenated solution of 3-bromo-5-thiophen-3-yl-pyridine (2.50 g, 10.4 mmol, 1 equiv), 1-(t-butyloxycarbonyl)-3-indoleboronic acid (4.073 g, 15.6 mmol, 1.50 equiv), Pd(PPh3)4 (601 mg, 0.520 mmol, 0.0500 equiv), and 2.0 M Na2CO3 (10.4 mL, 20.8 mmol, 2.00 equiv) in dioxane (120 ml) was heated under argon at reflux for 20 h. The reaction mixture was allowed to cool, then partitioned between water (500 mL) and ethyl acetate (3×150 mL). The combined organic layers were washed sequentially with water (500 mL) and brine (500 ml), then dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (40% ethyl acetate in hexane) to afford 3-(5-thiophen-3-yl-pyridin-3-yl)-1-(t-butyloxycarbonyl)-indole as a colorless oil. The oil was dissolved in ethyl acetate (100 ml), and the resulting solution was cooled to 0° C., then saturated with HCl gas. The solution was allowed to warm to 23° C. and stirred for 30 minutes. The precipitate was filtered and washed with ethyl ether (50 mL). The solid was then partitioned between ethyl acetate (150 mL) and aqueous saturated NaHCO3 solution (150 mL). The organic layer was dried over Na2SO4 and concentrated to give compound 1 (3-(5-thiophen-3-yl-pyridin-3-yl)-indole) as a white solid.

후처리

  1. temperatureat reflux for 20 h
  2. temperatureto cool
  3. custompartitioned between water (500 mL) and ethyl acetate (3×150 mL)
  4. washThe combined organic layers were washed sequentially with water (500 mL) and brine (500 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (40% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-18831cab961948f79d2a0e68818c6c77
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265403B1

반응 노트

불러오는 중…