Iodoethane → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1-ethyl-1H-indazol-5-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

HRID 879348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879348
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:15]=[C:14]([C:16]4[S:17][C:18]5[C:24]([C:25]6[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=6)=[C:23]([C@H:32]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:22]([CH3:43])=[CH:21][C:19]=5[N:20]=4)[CH:13]=[CH:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:51][CH3:52]>CN(C=O)C>[C:39]([O:38][C@@H:32]([C:23]1[C:22]([CH3:43])=[CH:21][C:19]2[N:20]=[C:16]([C:14]3[CH:13]=[CH:12][N:11]=[C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[N:1]([CH2:51][CH3:52])[N:2]=[CH:3]5)[CH:15]=3)[S:17][C:18]=2[C:24]=1[C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)[C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH3:42])([CH3:41])[CH3:40]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 86700148(S)-ethyl 2-(2-(2-(1H-indazol-5-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Produkt 1

HCID 86700147(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1-ethyl-1H-indazol-5-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-ethyl 2-(2-(2-(1H-indazol-5-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (32 mg, 0.052 mmol) in DMF (1 mL), was added Cs2CO3 (34 mg, 0.104 mmol), iodoethane (5 μL, 0.062 mmol). The reaction was reacted at room temperature. After the reaction finished, the reaction mixture was washed by water, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down, purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1-ethyl-1H-indazol-5-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate. LCMS-ESI+: calc'd for C36H35ClN4O3S: 639.2 (M+H+). found: 639.4;

Aufarbeitung

  1. customThe reaction was reacted at room temperature
  2. washthe reaction mixture was washed by water
  3. extractionextracted by EtOAc
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washeluting by 0-100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5d4a0c124fa342b4b8e9a65a916b0b27
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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