Hydrochloric Acid → HCID 21075903, 화합물

HRID 1373878노트

반응식

HRID 1373878 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]2.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:14]1[C:15]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]3)=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]1=2

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 220481596-Bromo-1-chloronaphthalen-2-ol

생성물 1

HCID 21075903HCID 21075903, 화합물수율 23.9%

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A mixture of 6-bromo-1-chloro-naphthalen-2-ol (11.2 g, 43.5 mmol), benzothiophene-2-boronic acid (15.1 g, 85.0 mmol) in three portions, palladium (II) acetate (0.76 g, 3.43 mmol) in three portions, potassium carbonate (30.1 g, 224 mmol) in three portions, tetrabutylammonium bromide (14.0 g, 43.5 mmol) in water (65 mL) and THF (40 mL) was heated at 70° C. for 8.5 hours. The reaction mixture was allowed to cool to ambient temperature and then poured into excess 2N hydrochloric acid. It was extracted with chloroform. The organic phase was then washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by flash chromatography using 100% chloroform, 30–50% 1,2-dichloroethane in hexane and 20–30% 1,2-dichloroethane in hexane (Biotage apparatus) eluent. Drying at 60° C. in vacuo for 20 minutes yielded 6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-ol as a beige-yellow solid (3.22 g, 23.9%) MP: 220–1° C.; Mass spectrum (−ES, [M−H]−) m/z 309/311. 1H NMR (500 MHz, DMSO-d6): δ 10.64 (s, 1H), 8.26 (d, 1H, J=1.73 Hz), 8.11 (d, 1H, J=8.85 Hz), 8.05 (dd, 1H, J=8.85 and 1.83 Hz), 7.95–8.01 (m, 2H), 7.87–7.92 (m, 2H), 7.33–7.43 ppm (m, 3H). Elemental Analysis for C18H11ClOS: Calcd: C, 69.56; H, 3.57; N, 0.00; Found: C, 69.58; H, 3.83; N, 0.00.

후처리

  1. temperatureto cool to ambient temperature
  2. extractionIt was extracted with chloroform
  3. washThe organic phase was then washed with water and brine
  4. dry with materialIt was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customThe residue was purified by flash chromatography
  8. customDrying at 60° C. in vacuo for 20 minutes

출처 및 근거

ORD 기록
ord-9b0ac81a2f324e9cbaaea8c626923e6a
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163954B2

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