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

HRID 1091870Notes

Reaction equation

HRID 1091870 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 11546334N9-(3,5-dichloro-4-pyridyl)-6-difluoromethoxybenzo[4,5]furo[3,2-c]pyridine-9-carboxamideYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a15b8eda8a524072a42c1bfb5893cd78
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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