Boron tribromide → Methyl 4-{[(4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

HRID 230005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230005
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22]C)=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([N:11]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[N:13]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68834931Methyl 4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

Produkt 1

HCID 68835422Methyl 4-{[(4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirring solution of the title compound of Example 14 Step C (1 mmol, 464 mg) in 5 mL of DCM at −78° C. under N2 was added dropwise BBr3 (5 mmol, 5 mL of a 1M solution in DCM). The reaction was allowed to warm to ambient temperature. After 15 min the reaction was poured into stirring NaHCO3 (gas evolution), and the product was extracted with DCM. The organic layer was dried with Na2SO4 and concentrated under reduced pressure, affording the product as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.90 (d, 2H), 7.44 (d, 2H), 7.28 (unres. m, 1H), 7.01 (d, 1H), 6.83 (dd, 1H), 4.64 (s, 2H), 3.89 (s, 3H), 3.58 (s, 3H), 3.20 (m, 1H), 2.10 (m, 2H), 1.89 (m, 2H), 1.59 (m, 2H), 0.98-1.14 (overlapping m, 3H), 0.86 (s, 9H). MS (ESI): m/z 450 (M+H). HPLC A: 2.30 min.

Aufarbeitung

  1. additionAfter 15 min the reaction was poured
  2. extractionthe product was extracted with DCM
  3. dry with materialThe organic layer was dried with Na2SO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-533fd74147ce466ba7813568b438e6d8
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563815B2

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