Bromine → methyl 4-(4-(5-bromothiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate

HRID 415951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415951
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[Br:22]Br>CN(C=O)C>[Br:22][C:5]1[S:1][C:2]([C:6]2([C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=3)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 24408Bromine2×HCID 59160841Methyl 4-(4-(thiazol-2-yl)-tetrahydro-2h-pyran-4-yl)benzoate

Produkt 1

HCID 66619354methyl 4-(4-(5-bromothiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To the mixture of methyl 4-(4-(thiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate (570 mg, 1.88 mmol) in DMF (5 mL) was added a 1M solution of bromine in DMF (1.9 mL, 1.88 mmol). After 2 hours, additional 1M solution of bromine in DMF (1.9 mL, 1.88 mmol) was added. The reaction mixture was then concentrated to half its volume and poured into water (25 mL). The resulting solid was filtered and washed with water and dried to give methyl 4-(4-(5-bromothiazol-2-yl)-tetrahydro-2H-pyran-4-yl)benzoate. 1H NMR (400 MHz, dmso-d6): δ 7.99 (d, J=8.0 Hz, 2H); 7.58 (s, 1H); 7.41 (d, J=8.0 Hz, 2H); 3.87 (s, 3H); 3.91-3.84 (m, 2H); 3.73-3.68 (m, 2H); 2.63-2.59 (m, 2H); 2.41-2.37 (m, 2H); MS found for C16H16BrNO3S (m/z): 3840.3 [M++1].

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated to half its volume
  2. additionpoured into water (25 mL)
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4ee1231d2d994fc1adf2d3641c092585
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088771B2

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