Lithium Hydroxide → [4-(4-Methoxy-4''-trifluoromethoxy-[1,1';3',1'']terphenyl-5'-ylmethoxy)-2-methyl-phenoxy]-acetic acid

HRID 19503

반응식

HRID 19503 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25]C)=[C:20]([CH3:27])[CH:19]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[F:28][C:29]([F:41])([F:40])[O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[C:42](=[O:45])([O-])[O-:43].[K+].[K+].[OH-].[Li+]>O1CCOCC1.C1(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)C=CC=CC=1.C(O)C.O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:5]=[C:4]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:42]([OH:43])=[O:45])=[C:20]([CH3:27])[CH:19]=3)[CH:3]=[C:2]([C:34]3[CH:35]=[CH:36][C:31]([O:30][C:29]([F:41])([F:40])[F:28])=[CH:32][CH:33]=3)[CH:7]=2)=[CH:13][CH:12]=1

참가 물질

9

반응물 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 691074205-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4'-methoxy-biphenyl

생성물 1

HCID 11599107[4-(4-Methoxy-4''-trifluoromethoxy-[1,1';3',1'']terphenyl-5'-ylmethoxy)-2-methyl-phenoxy]-acetic acid

시약·촉매·용매 4

HCID 178420554HCID 178420554, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

5-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4′-methoxy-biphenyl 15 (50 mg, 0.11 mmol) and 4-trifluoromethoxyphenylboronic acid (30 mg, 0.15 mmol, 1.3 equiv.) are dissolved in dioxane (0.5 mL). Potassium carbonate (38 mg, 0.27 mmol), water (0.05 mL) and ethanol (0.05 mL) are added, followed by tetrakis (triphenylphosphino)palladium (15.6 mg, 0.13 mmol). The mixture is stirred under nitrogen and subjected to microwave (170° C. for 10 min). Cooling, addition of 0.25 mL of aqueous 1N lithium hydroxide solution, and stirring for 3 hours at room temperature, followed by reversed-phase purification yielded [4-(4-methoxy-4″-trifluoromethoxy-[1,1′;3′,1″]terphenyl-5′-ylmethoxy)-2-methyl-phenoxy]-acetic acid A2. 1H-NMR (400 MHz, CDCl3) δ=7.50 (m, 3H), 7.42 (m, 4H), 7.17 (d, J=8.0 Hz, 2H), 6.87 (d, J=8.0 Hz, 2H), 6.75 (d, J=2.8 Hz, 1H), 6.65 (dd, J=8.8, 2.8 Hz, 1H), 6.58 (d, J=8.8 Hz, 1H), 5.17 (s, 2H), 4.50 (s, 2H), 3.73 (s, 3H), 2.16 (s, 3H). 19F-NMR (376 MHz, CDCl3) δ=−57.8. MS calculated for C30H26F3O6 (M+H+) 539.17. found 539.0.

후처리

  1. custom(170° C. for 10 min)
  2. temperatureCooling
  3. stirringstirring for 3 hours at room temperature
  4. customfollowed by reversed-phase purification

출처 및 근거

ORD 기록
ord-23ddb7be655f4c35a298c86d3c047f61
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745445B2

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