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Potassium Carbonate → 7'-(5-Chloropyridin-3-yl)-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

HRID 1468237
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HRID 1468237 반응식
Br[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][CH2:7][C:8]3([C:11]42[N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[N:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:19]=[C:18]3[C:5]([CH2:6][CH2:7][C:8]4([C:11]53[N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]5)[CH2:9][CH2:10]4)=[CH:4][CH:3]=2)[CH:24]=[N:25][CH:26]=1
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7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 201118775-Chloropyridine-3-boronic acidHCID 727146587'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

생성물 1

HCID 727147457'-(5-Chloropyridin-3-yl)-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine수율 37.7%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6344Dichloromethane용매

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온도
130 °C

실험 절차

A mixture of 7′-bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 1, 100 mg, 0.31 mmol), 5-chloropyridin-3-ylboronic acid (74 mg, 0.47 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride (23 mg, 0.03 mmol), aq. potassium carbonate (2 M, 0.31 mL, 0.63 mmol) and 1,4-dioxane (1 mL) were mixed in a vial and heated in a microwave reactor at 130° C. for 30 min. When cooled to r.t., the mixture was diluted with DCM, washed with water and dried over Na2SO4. The filtrate was concentrated and the product purified by preparative HPLC to give the title compound (41 mg, 37% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.10 (m, 2 H), 0.24 (m, 1 H), 0.55 (m, 1 H), 1.51 (dt, 1 H), 2.18 (s, 3 H), 2.39 (m, 1 H), 3.01 (m, 2 H), 6.52 (br. s., 2 H), 6.74 (d, 1 H), 7.30 (d, 1 H), 7.52 (dd, 1 H), 7.97 (s, 1 H), 8.57 (d, 1 H), 8.61 (d, 1 H); MS (APCI+) m/z 351 [M+H]+.

후처리

  1. additionwere mixed in a vial and
  2. temperatureWhen cooled to r.t.
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtrate was concentrated
  6. customthe product purified by preparative HPLC

출처 및 근거

ORD 기록
ord-d83d89cefc884b7abcaee1662f3a7302
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000184B2

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