1,4-Dibromobutane → 6-(N-(4-bromobutyl)methylsulfonamido)-5-iodo-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

HRID 2190196Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-iodo-N-methyl-6-(methylsulfonamido)-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide (crude ˜20%) (400 mg, 0.824 mmol) was added 1,4-dibromobutane (1780 mg, 8.24 mmol) and CESIUM CARBONATE (537 mg, 1.648 mmol) and DMF (4 ml) Heated at 120° C. 30 min. Added water and extracted with EtOAc. Conc. on vac to oil. Added 3 mL ACN and 1 mL water. Filtered with 0.45p filter Purified via HPLC C8 40-80% ACN/H2O (0.1% NH4OH) 40 mL/min over 10 min. to give 6-(N-(4-bromobutyl)methylsulfonamido)-5-iodo-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

Workup

custom30 min
extractionAdded water and extracted with EtOAc
additionAdded 3 mL ACN and 1 mL water
filtrationFiltered with 0.45p
filtrationfilter
customPurified via HPLC C8 40-80% ACN/H2O (0.1% NH4OH) 40 mL/min over 10 min.

Sources & evidence

ORD record: ord-33f8d25ed32d45cdb4d23cc240c40399
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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