Cesium carbonate → 6-(N-(2-chlorophenethyl)methylsulfonamido)-5-iodo-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

HRID 2190194Notes

Reaction equation

HRID 2190194 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[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:36].C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][CH2:28][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

4

Reactant 3

HCID 10796Cesium carbonate2×HCID 27569631-(2-Bromoethyl)-2-chlorobenzeneHCID 580523565-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

Product 1

HCID 580524426-(N-(2-chlorophenethyl)methylsulfonamido)-5-iodo-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

Conditions

Temperature
150 °C

Procedure

To 5-iodo-N-methyl-6-(methylsulfonamido)-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide (150 mg, 0.309 mmol) was added 1-(2-bromoethyl)-2-chlorobenzene (678 mg, 3.09 mmol) and CESIUM CARBONATE (101 mg, 0.309 mmol) was heated at 150° C. μwave 10 min. LCMS showed 1:1 SM/Prod and 1:2 styrene/Br. Added CESIUM CARBONATE (101 mg, 0.309 mmol) and heated additional 10 min at 150° C. μwave. Added water and extracted with EtOAc. Conc. on vac. Added ACN/water and filtered with 0.45 μPTFE filter

Workup

  1. extractionAdded water and extracted with EtOAc
  2. filtrationAdded ACN/water and filtered with 0.45 μPTFE
  3. filtrationfilter

Sources & evidence

ORD record
ord-e8961f81035d48b08f4bf9c1f3b18d25
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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