1,2-Dichloroethane → 4-Bromo-N-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxamide

HRID 1987920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987920
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[NH:5][CH:6]=1.[NH2:10][C:11]1[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[C:13]([O:23][CH3:24])[CH:12]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>ClC(Cl)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:10][C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([OH:19])([CH3:20])[CH3:18])=[C:13]([O:23][CH3:24])[CH:12]=2)=[O:9])[NH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27413814-bromo-1H-pyrrole-2-carboxylic acidHCID 595950521-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

Produkt 1

HCID 672152534-Bromo-N-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxamideAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-1H-pyrrole-2-carboxylic acid (1.00 g, 5.30 mmol), preparation described in step A of Example 2, and 1-(4-amino-2-methoxyphenoxy)-2-methylpropan-2-ol (1.12 g, 5.30 mmol), preparation described in step A of Example 4. in dichloroethane (46.0 mL) was added EDC (2.03 g, 10.6 mmol) and HOBT (1.62 g, 10.6 mmol) and the reaction was allowed to stir at rt for 16 h. The reaction mixture was diluted with EtOAc (100 mL), washed with sat. NaHCO3 (3×100 mL), water, brine, dried over anhydrous Na2SO4 and concentrated to give 1.84 g of the title compound as a brown oil which was used in the next step without purification: HPLC a) column: Phenomenex Luna 5μ 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% H3PO4 to 90% MeOH/10% H2O/0.1% H3PO4; 1 min hold, 4 mL/min UV detection at 220 nm, 3.058 min retention time, (91%); HPLC b) column: Phenomenex Luna C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 3.051 min retention time; MS (ES) 385 [M+H]+.

Aufarbeitung

  1. washwashed with sat. NaHCO3 (3×100 mL), water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-71b4a0b2807c4f8a841fa85edd0a6e4b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553836B2

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