Benzenamine, 3,5-bis(trifluoromethyl)- → 2-[5-(3,5-Bis-trifluoromethyl-phenylamino)-4'-chloro-3'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester

HRID 226539

반응식

HRID 226539 반응식
[CH3:1][O:2][C:3](=[O:34])[CH:4]([C:9]1[CH:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[F:35][C:36]([F:49])([F:48])[C:37]1[CH:38]=[C:39]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[NH2:40].CC(C)([O-])C.[Na+].C(P(C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3](=[O:34])[CH:4]([C:9]1[CH:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:31])[F:32])[CH:24]=2)[CH:12]=[C:13]([NH:40][C:39]2[CH:38]=[C:37]([C:36]([F:48])([F:49])[F:35])[CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:41]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

참가 물질

7

반응물 4

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 23676156Sodium t-butoxideHCID 577549642-(4'-Chloro-5-trifluoromethanesulfonyloxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester

생성물 1

HCID 577550562-[5-(3,5-Bis-trifluoromethyl-phenylamino)-4'-chloro-3'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester수율 45.8%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매2회

실험 절차

A mixture of 2-(4′-chloro-5-trifluoromethanesulfonyloxy-3′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester (48 mg, 0.10 mmol), 3,5-bis-(trifluoromethyl)-aniline (18 μL, 0.12 mmol), sodium tert-butoxide (9.8 mg, 0.10 mmol), Pd(OAc)2 (2.5 mg, 0.01 mmol), 2-(di-tert-butylphoshino-1,1′-binaphthyl (3.5 mg, 0.01 mmol) and toluene (1 mL) was stirred under microwave irradiation at 130° C. for 3×10 min. The mixture was diluted with toluene (9 mL), washed with 1M HCl (2×10 mL) and brine (10 mL), dried (MgSO4), concentrated in vacuo and purified by flash column chromatography (diethylether-petroleum ether) to afford the title product as a colourless powder (28 mg, 44%). Mass spectrum (ESI, m/z): 610, 612 (M−H).

후처리

  1. washwashed with 1M HCl (2×10 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by flash column chromatography (diethylether-petroleum ether)

출처 및 근거

ORD 기록
ord-f17439eb2c694957a946408cc6238aa7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557244B2

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