Acetic Acid → N9-(3,5-dichloro-4-pyridyl)-6-difluoromethoxybenzo[4,5]furo[3,2-c]pyridine-9-carboxamide

HRID 1091870

Reaktionsgleichung

Reaktionsgleichung von HRID 1091870
[F:1][CH:2]([F:29])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[C:8]=2[C:7]([C:17]([O:19]C2C=CC([N+]([O-])=O)=CC=2)=O)=[CH:6][CH:5]=1.[NH2:30][C:31]1[C:36]([Cl:37])=[CH:35][N:34]=[CH:33][C:32]=1[Cl:38].[H-].[Na+].C(O)(=O)C>CN(C=O)C.O>[Cl:38][C:32]1[CH:33]=[N:34][CH:35]=[C:36]([Cl:37])[C:31]=1[NH:30][C:17]([C:7]1[C:8]2[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:4]([O:3][CH:2]([F:29])[F:1])=[CH:5][CH:6]=1)=[O:19]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 593961534-Nitrophenyl 6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate

Produkt 1

HCID 11546334N9-(3,5-dichloro-4-pyridyl)-6-difluoromethoxybenzo[4,5]furo[3,2-c]pyridine-9-carboxamideAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a well stirred solution of 4-Nitrophenyl 6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate (6.0 mg, 0.015 moles) and 4-amino-3,5-dichloropyridine (4.9 mg, 0.030 moles) in DMF (50.0 mL) was added sodium hydride (60% dispersion in mineral oil) (900 mg, 0.0225 moles) at −5° C. and stirred for 30-40 minutes. Excess of DMF was removed under reduce pressure, the residue obtained was diluted with water (500 mL) and acidified to pH 5-6 with acetic acid. The solid obtained was filtered, washed with water and dried to afford crude product (5.6 g). Purification thorough silica gel column using 25 Methanol in chloroform as eluent gave 2.7 g product as off-white solid.

Aufarbeitung

  1. customExcess of DMF was removed
  2. customthe residue obtained
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. customto afford crude product (5.6 g)
  8. customPurification thorough silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-a15b8eda8a524072a42c1bfb5893cd78
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129401B2

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