Sodium Carbonate → 4-(2'-Bromo-4'-methylbiphenyl-4-yl)-1-(2,2,2-trifluoroethyl)piperidine

HRID 340634노트

반응식

HRID 340634 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1I.CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]([F:34])([F:33])[F:32])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.CC#N>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:18]1[CH:19]=[CH:20][C:21]([CH:24]2[CH2:25][CH2:26][N:27]([CH2:30][C:31]([F:34])([F:32])[F:33])[CH2:28][CH2:29]2)=[CH:22][CH:23]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 6266343-Bromo-4-iodotolueneHCID 690240014-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-(2,2,2-trifluoroethyl)piperidine

생성물 1

HCID 690259234-(2'-Bromo-4'-methylbiphenyl-4-yl)-1-(2,2,2-trifluoroethyl)piperidine

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of 2-bromo-1-iodo-4-methylbenzene (0.764 g, 2.57 mmol), the title compound from Example 60 Step B (1.00 g, 2.71 mmol), dichloro bis(triphenylphosphine)palladium(II) (0.095 g, 0.135 mmol), sodium carbonate (5.42 mL of 1 M solution, 5.42 mmol) and MeCN (5.42 mL) was heated at 110° C. overnight. Organic layer was separated. Aqueous layer was extracted with hexanes-EtOAc. The organic layers were combined and concentrated. Silica gel flash chromatography eluting with hexanes:EtOAc (20:1 to 9:1 v/v) gave the title compound: LCMS m/z 414.0 [M+H+]; 1H NMR (500 MHz, CDCl3) δ 7.54 (s, 1 H),7.40 (d, J=8.1 Hz, 2 H), 7.31 (d, J=8.1 Hz, 2 H),7.26 (d, J=7.8 Hz, 1 H),7.20 (d, J=7.8 Hz, 1 H),3.16 (m, 2 H), 3.08 (q, J=9.8 Hz, 2 H),2.57 (m, 3 H),2.42 (s, 3 H).1.95-1.88 (m, 4 H).

후처리

  1. customOrganic layer was separated
  2. extractionAqueous layer was extracted with hexanes-EtOAc
  3. concentrationconcentrated
  4. washSilica gel flash chromatography eluting with hexanes:EtOAc (20:1 to 9:1 v/v)

출처 및 근거

ORD 기록
ord-730c1701cb624e3c919fef31c05fc710
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895583B2

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