5-Bromothiophene-2-sulfonyl chloride → HCID 86603939, compound

HRID 1244241Notes

Reaction equation

HRID 1244241 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C:10]([NH2:22])([N:19]([CH3:21])[CH3:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1>N1C=CC=CC=1.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C:10]([NH:22][S:29]([C:27]2[S:28][C:24]([Br:23])=[CH:25][CH:26]=2)(=[O:31])=[O:30])([N:19]([CH3:20])[CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 69544952HCID 69544952, compound

Product 1

HCID 86603939HCID 86603939, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled solution of the intermediate D3 (2.0 g, 0.0065 moles) in dry pyridine was added dropwise a solution of 5-bromothiophene-2-sulfonyl chloride (1.88 g, 0.0072 moles) in dichloromethane. The mixture was stirred for 1 hour at room temperature. The mixture was evaporated to dryness then purified by chromatography over silica, eluting with hexane up to 50% EtOAc/hexane, affording the title compound D6 as a brown solid (2.1 g, 90%). M-H 532. 1H NMR: δ MeOD 1.45 (9H,s), 2.76 (2H, m), 3.02 (2H, m), 3.30 (6H,s), 3.48 (2H, m), 3.58 (2H, m), 6.47 (1H, s), 7.26 (2H, m), 7.76 (1H, s).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthen purified by chromatography over silica
  3. washeluting with hexane up to 50% EtOAc/hexane

Sources & evidence

ORD record
ord-9cd8bd3da4f94a5ea23a728070f8d3e6
Source dataset
uspto-grants-2006_10
Patent number
US07122538B2

Reaction notes

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