2-Formyl-4-(tributylstannyl)thiazole → 4-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehyde

HRID 1403760

반응식

HRID 1403760 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.C([Sn](CCCC)(CCCC)[C:31]1[N:32]=[C:33]([CH:36]=[O:37])[S:34][CH:35]=1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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:31]4[N:32]=[C:33]([CH:36]=[O:37])[S:34][CH:35]=4)=[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

5

반응물 2

HCID 164271112-Formyl-4-(tributylstannyl)thiazoleHCID 21952018(4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine

생성물 1

HCID 219519814-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehyde수율 44%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

Prepared according to Procedure B from (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (2 g, 4.56 mmol), 4-(tributylstannyl)thiazole-2-carbaldehyde (1.84 g, 4.56 mmol) and dichlorobis(triphenylphosphine)palladium (II) (0.74 g, 20 mol %) heated at reflux overnight (18 hrs) in dioxane (50 ml). The cooled solution was filtered through a plug of Celite®, concentrated and triturated with iso-hexane (3×20 ml). The resultant solid was purified via flash column chromatography on silica gel, eluting with 5% methanol in chloroform. The purified product was isolated as a yellow solid (0.85 g, 44%). δ H [2H6] DMSO 10.10 (1H, s), 9.30 (1, bs), 8.90 (1 Hs), 8.50 (2H, s&d), 8.45 (1H, d), 8.20 (1H, d), 7.40 (5H, bm), 7.10 (4H, 2d), 6.80 (1H, d).

후처리

  1. customPrepared
  2. temperatureheated
  3. filtrationThe cooled solution was filtered through a plug of Celite®
  4. concentrationconcentrated
  5. customtriturated with iso-hexane (3×20 ml)
  6. customThe resultant solid was purified via flash column chromatography on silica gel
  7. washeluting with 5% methanol in chloroform

출처 및 근거

ORD 기록
ord-e4653749cfc74e048bde07356d9e04a8
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912205B2

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