Cesium carbonate → N-[[(3S,3aS)-7-(2-methylsulfonylphenyl)-1-oxo-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-3-yl]methyl]-5-chlorothiophene-2-carboxamide

HRID 1050224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050224
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21](B5OC(C)(C)C(C)(C)O5)=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:33])[O:12]2)=[O:8])=[CH:4][CH:3]=1.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1Br)(=[O:37])=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+]>[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>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21]([C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=5[S:35]([CH3:34])(=[O:37])=[O:36])=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:33])[O:12]2)=[O:8])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 190318Benzene, 1-bromo-2-(methylsulfonyl)-HCID 1317360535-chloro-N-(((3S,3 aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide

Produkt 1

HCID 118574663N-[[(3S,3aS)-7-(2-methylsulfonylphenyl)-1-oxo-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-3-yl]methyl]-5-chlorothiophene-2-carboxamideAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator

Versuchsvorschrift

Using compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (the product of step (b) in Example 35) (50 mg, 0.102 mmol), o-methylsulfonylbromobenzene (29 mg, 0.122 mmol), tetrakis (triphenylphosphine) palladium (12 mg, 0.010 mmol), and cesium carbonate (66 mg, 0.204 mmol) as starting materials, preparation following the method as described in Example 35 (c) afforded off-white solid 19 mg, yield: 35.2%.

Aufarbeitung

  1. custommaterials, preparation

Quellen und Nachweise

ORD-Eintrag
ord-63b99377bf65496fbe3f2ee9b3c54596
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382265B2

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