1,4-Dibromobutane → HCID 58052535, compound

HRID 2190163Notes

Reaction equation

HRID 2190163 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:11]([CH2:14][CH3:15])[CH:12]=2)[O:7][C:6]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:4].[Br:28][CH2:29][CH2:30][CH2:31][CH2:32]Br.C(=O)([O-])[O-].[Cs+].[Cs+].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CC(N(C)C)=O.O>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:16]([CH2:32][CH2:31][CH2:30][CH2:29][Br:28])[S:17]([CH3:20])(=[O:19])=[O:18])=[C:11]([CH2:14][CH3:15])[CH:12]=2)[O:7][C:6]=1[C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)=[O:4]

Participants

7

Reactant 4

HCID 80561,4-DibromobutaneHCID 10796Cesium carbonateHCID 180504Ceric ammonium nitrateHCID 58052326HCID 58052326, compound

Product 1

HCID 58052535HCID 58052535, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

5-Ethyl-2-(4-fluoro-phenyl)-6-methanesulfonylamino-furo[2,3-b]pyridine-3-carboxylic acid methylamide (60 mg, 0.153 mmol), 1,4-dibromobutane (662 mg, 3.07 mmol) and cesium carbonate (52.4 mg, 0.161 mmol) in DMA (766 μL) are heated for 15 min at 120° C. by microwave. 1 mL CAN and 0.5 mL water are added and the mixture is filtered with a 0.45μ PTFE filter. Purification is achieved by reverse phase HPLC with a C8 column with 20-100% CAN//H2O (0.1% TFA) over 15 min with 5 min hold to give 6-[(4-Bromo-butyl)-methanesulfonyl-amino]-5-ethyl-2-(4-fluoro-phenyl)-furo[2,3-b]pyridine-3-carboxylic acid methylamide (40.1 mg, 50%) MS (ESI) m/z 527.8 (M+1). Retention time=1.78 min, Method A.

Workup

  1. filtrationthe mixture is filtered with a 0.45μ PTFE
  2. filtrationfilter
  3. customPurification

Sources & evidence

ORD record
ord-3234ebcb31e24858903f614ca0efc140
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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