Cesium fluoride → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)vinyl)thiazolo[5,4-b]pyridine

HRID 1177493

반응식

HRID 1177493 반응식
[F-].[Cs+].[O:3]1[CH2:8][CH2:7][CH2:6][O:5][CH:4]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[C:22]([N:23]=2)=[CH:21][CH:20]=[C:19](Cl)[N:18]=3)=[C:11]([F:25])[CH:10]=1.[CH2:26]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([Sn](CCCC)(CCCC)CCCC)=[CH2:41])=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.CC(=O)OCC.[Cu]I.[Pd].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.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>[O:3]1[CH2:8][CH2:7][CH2:6][O:5][CH:4]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[C:22]([N:23]=2)=[CH:21][CH:20]=[C:19]([C:40]([C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:35][CH:36]=2)=[CH2:41])[N:18]=3)=[C:11]([F:25])[CH:10]=1

참가 물질

8

반응물 3

HCID 25953Cesium fluorideHCID 18436367{1-[4-(Benzyloxy)phenyl]ethenyl}(tributyl)stannaneHCID 591748622-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine

생성물 1

HCID 671114382-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)vinyl)thiazolo[5,4-b]pyridine

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
55 °C

실험 절차

A slurry of cesium fluoride (0.325 g, 2.14 mmol), CuI 0.0271 g, 0.143 mmol), tetrakis(triphenylphosphine) palladium (0) (0.0824 g, 0.0713 mmol), 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (0.500 g, 1.43 mmol), and crude (1-(4-(benzyloxy)-phenyl)vinyl)tributylstannane (1.07 g, 2.14 mmol) in 5 mL DMF was flushed with argon, sealed, and heated to 55° C. overnight. The reaction mixture was diluted with EA, filtered through celite, rinsing with EA. The filtrate was washed with water, brine, dried over sodium sulfate, filtered, and concentrated. The residue was adsorbed onto 4 g silica gel from DCM, concentrated, and purified by ISCO 40 g, 0-100% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)vinyl)thiazolo[5,4-b]pyridine as an orange solid. MS (ESI) m/z: calculated: 524.2; Observed: 525.1 (M++1).

후처리

  1. customsealed
  2. filtrationfiltered through celite
  3. washrinsing with EA
  4. washThe filtrate was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationconcentrated
  9. custompurified by ISCO 40 g, 0-100% EA/hexanes

출처 및 근거

ORD 기록
ord-ab63040e05d24648a271a578f48bba7e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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