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Dichloromethane → 6-(5-Hydroxy-benzofuran-2-yl)-nicotinamide

HRID 501044
Notes
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Reaction equation

HRID 501044 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=3)=[CH:8][C:7]=2[CH:20]=1.C(Cl)Cl.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=3)=[CH:8][C:7]=2[CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 250149326-(5-Methoxy-benzofuran-2-yl)-nicotinamide

Product 1

HCID 250148426-(5-Hydroxy-benzofuran-2-yl)-nicotinamide

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

6-(5-Methoxy-benzofuran-2-yl)-nicotinamide (0.25 mmol) was mixed with CH2Cl2 (3 mL) at 0° C. under argon atmosphere. BBr3 (1M in CH2Cl2) (1.0 mL) was added dropwise and the mixture was stirred for 2 h at rt. The mixture was hydrolysed with H2O followed by NaHCO3 (sat. aq.). The resulting mixture was filtered, and the obtained precipitate was washed with H2O and EtOAc. The solid was dried at 40° C. for 15 h under vacuum (12 mg).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe obtained precipitate was washed with H2O and EtOAc
  3. customThe solid was dried at 40° C. for 15 h under vacuum (12 mg)

Sources & evidence

ORD record
ord-4a69051431f14f34b8091a5b3b6ea992
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772256B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes