1-Bromo-2-iodobenzene → 4-(2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528552

Reaktionsgleichung

Reaktionsgleichung von HRID 528552
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=1I.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=1[N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:21]=[C:12]([S:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]1=2

Komponenten

7

Edukt 4

HCID 114151-Bromo-2-iodobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Produkt 1

HCID 897618114-(2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A microwave vial was charged with INTERMEDIATE M (0.100 g, 0.240 mmol), Xantphos (0.028 g, 0.048 mmol), 1-bromo-2-iodobenzene (0.045 mL, 0.359 mmol), Pd2(dba)3 (0.022 g, 0.024 mmol) and sodium tert-butoxide (0.046 g, 0.479 mmol). The mixture was diluted with toluene (2.395 mL), and purged with nitrogen, and stirred at 130° C. in the microwave for 20 minutes. After completion, the reaction was diluted with water, and washed with DCM. The organics were dried via phase separator, and concentrated under a vacuum. The material was then purified via 2 g SCX column. The material was concentrated to provide 4-(2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide, which was taken forward without further purification.

Aufarbeitung

  1. custompurged with nitrogen
  2. additionAfter completion, the reaction was diluted with water
  3. washwashed with DCM
  4. customThe organics were dried via phase separator
  5. concentrationconcentrated under a vacuum
  6. customThe material was then purified via 2 g SCX column
  7. concentrationThe material was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-478cadaf8ba8403ab7797eb21166cf5b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346798B2

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