Sodium Hydroxide → 5-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)thiazole-4-carbaldehyde

HRID 51125

반응식

HRID 51125 반응식
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21](I)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]1CCO[CH:27]1[C:31]1[N:32]=[CH:33][S:34][C:35]=1[Sn](CCCC)(CCCC)CCCC.[OH-].[Na+]>C1COCC1.Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ag]=O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:35]4[S:34][CH:33]=[N:32][C:31]=4[CH:27]=[O:26])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 3

HCID 14798Sodium HydroxideHCID 21952018(4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amineHCID 219520694-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole

생성물 1

HCID 542040185-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)thiazole-4-carbaldehyde수율 40.9%

시약·촉매·용매 4

HCID 92152Silver(II) oxide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

Prepared according to Procedure B from (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (0.876 g, 2 mmol), 4-(1,3-dioxolan-2-yl)-5-tributylstannylthiazole (2.1 mmol), bis (triphenylphosphine) palladium (II) chloride (0.105 g, 0.15 mmol, 7.5 mol %) and silver oxide (0.463 g, 2 mmol) heated under reflux under nitrogen for 18 hr. The reaction mixture was then filtered through Harborlite® and the filtrate was concentrated. The product was purified on Bond Elut™ cartridge, eluting sequentially with dichloromethane, chloroform, diethyl ether and ethyl acetate. The ketal (0.385 g, 0.824 mmol) was stirred at room temperature in a mixture of THF (10 ml) and 1 N HCl (10 ml) for 2 hr. The suspension was basified with 2N NaOH (5 ml) and the THF was removed. The aqueous suspension was filtered and washed with water to give the product as a yellow solid (0.346 g);m/z 424.

후처리

  1. customPrepared
  2. temperatureheated
  3. temperatureunder reflux under nitrogen for 18 hr
  4. filtrationThe reaction mixture was then filtered through Harborlite®
  5. concentrationthe filtrate was concentrated
  6. customThe product was purified on Bond Elut™ cartridge
  7. washeluting sequentially with dichloromethane, chloroform, diethyl ether and ethyl acetate
  8. customthe THF was removed
  9. filtrationThe aqueous suspension was filtered
  10. washwashed with water

출처 및 근거

ORD 기록
ord-99a655602e0f4779a892e238c563e63b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713485B2

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