1,2-Dimethoxyethane → 3-(6-Methoxy-1-(methoxymethoxy)-3-methyl-naphthalen-2-yl)-thiophene

HRID 1992961노트

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HRID 1992961 반응식
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[C:3]=1[O:15][CH2:16][O:17][CH3:18].[S:19]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20]1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)C.C1(P([Pd-4](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)C=CC=CC=1>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]([O:15][CH2:16][O:17][CH3:18])=[C:2]([C:21]1[CH:22]=[CH:23][S:19][CH:20]=1)[C:11]([CH3:12])=[CH:10]2

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

생성물 1

HCID 685377683-(6-Methoxy-1-(methoxymethoxy)-3-methyl-naphthalen-2-yl)-thiophene

시약·촉매·용매 2

HCID 178420553HCID 178420553, 화합물촉매HCID 3283Diethyl Ether용매

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온도
160 °C

실험 절차

2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14) (0.35 g, 1.12 mmol), thiophene 3-boronic acid (0.359 g, 2.81 mmol), tetrakis(triphenylphosphino)palladium (0) (0.031 g, 0.027 mmol), 2 M sodium carbonate (4 mL) and ethylene glycol dimethyl ether (4 mL) were added in a sealed tube and heated at 160° C. for 20 min. Reaction mixture was cooled to room temperature then diluted with diethyl ether. The mixture was washed with water followed by brine, dried over Na2SO4, filtered and concentrated. The crude material purified with a gradient of 1% EtOAc to 4% EtOAc in hexanes over 45 min to afford the title compound (199) as oil, 0.347 g, (98%). 1H NMR (400 MHz, d-CDCl3): δ 2.29 (s, 3H), 3.23 (s, 3H), 3.93 (s, 3H), 4.76 (s, 2H), 7.06-7.07 (m, 1H), 7.10-7.15 (m, 2H), 7.25-7.26 (m, 1H), 7.40-7.42 (m, 2H), 8.04 (d, J=9.2 Hz, 1H).

후처리

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. washThe mixture was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material purified with a gradient of 1% EtOAc to 4% EtOAc in hexanes over 45 min

출처 및 근거

ORD 기록
ord-f53bd4d571a94fd2a825ec539686163f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649093B2

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