3-Chlorobenzenesulphonyl chloride → HCID 68323886, compound

HRID 573573Notes

Reaction equation

HRID 573573 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=3)[C:3]=12.CC(C)([O-])C.[Na+].[Cl:30][C:31]1[CH:32]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1>C1COCC1.CN(C=O)C>[Br:23][C:19]1[CH:18]=[C:17]([C:16]2[C:3]3[C:4](=[N:5][C:6]([CH3:13])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]=3[NH:1][S:37]([C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([Cl:30])[CH:32]=3)(=[O:39])=[O:38])[S:14][CH:15]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23676156Sodium t-butoxideHCID 68324059HCID 68324059, compound

Product 1

HCID 68323886HCID 68323886, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-amino-3-(3-bromophenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 46) (2.87 g, 7.33 mmol) in THF (30 mL) and DMF (15 mL) was added sodium tert-butoxide (1.762 g, 18.34 mmol) and 3-chlorobenzenesulfonyl chloride (2.066 mL, 14.67 mmol). The reaction mixture was then stirred at RT under nitrogen for ca. 30 min and then quenched with saturated ammonium chloride solution (ca. 60 mL). The mixture was extracted with DCM (ca. 30 mL×5) and the combined organics dried and concentrated in vacuo. Purification by chromatography on silica, eluting with a gradient of 0-50% ethyl acetate in DCM afforded the title compound (1.48 g). LCMS (A) m/z: 566/568 [M+1]+, Rt 1.47 min (acidic).

Workup

  1. customquenched with saturated ammonium chloride solution (ca. 60 mL)
  2. extractionThe mixture was extracted with DCM (ca. 30 mL×5)
  3. customthe combined organics dried
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica
  6. washeluting with a gradient of 0-50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-691387002e4d4cabb48a051e279484a0
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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