4-Nitrophenol → 4-Nitrophenyl 6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate

HRID 548996

Reaction equation

HRID 548996 reaction equation
[F:1][CH:2]([F:20])[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]([OH:19])=[O:18])=[CH:6][CH:5]=1.[CH:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[C:23](O)[CH:22]=1.CCN=C=NCCCN(C)C.Cl.CC1(C)C=CN=C(N)C1>CN(C=O)C>[F:20][CH:2]([F:1])[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][C:23]2[CH:22]=[CH:21][C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=2)=[O:18])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593961556-(Difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carboxylic acidHCID 665922284,4-Dimethyl amino pyridine

Product 1

HCID 593961534-Nitrophenyl 6-difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of 6-Difluoromethyloxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylic acid (5.5 g, 0.0197 moles), p-nitro phenol (4.1 g, 0.0295 moles), EDCl (5.7 g, 0.295 moles), 4,4-dimethyl amino pyridine (250 mg, 0.00197 moles) in DMF (603.0 mL) was heated to 70-75° C. for 4-5 hours. The residue obtained after removal of solvent under vacuo was triturated with water (50.0 mL) to give intermediate-18 (6.0 mg) as yellow solid.

Workup

  1. customThe residue obtained
  2. customafter removal of solvent under vacuo
  3. customwas triturated with water (50.0 mL)
  4. customto give intermediate-18 (6.0 mg) as yellow solid

Sources & evidence

ORD record
ord-da68c2edf9074921a8c1a09097e8558a
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Linked notes

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