Ammonium Chloride → HCID 18518542, compound

HRID 1369115Notes

Reaction equation

HRID 1369115 reaction equation
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[Li]C(C)(C)C.[CH2:16]([N:18]([CH2:33][CH3:34])[CH2:19][CH2:20][N:21]1[C:31]2[C:26](=[C:27]([Br:32])[CH:28]=[CH:29][CH:30]=2)[C:24](=[O:25])[C:22]1=[O:23])[CH3:17].[NH4+].[Cl-]>C1COCC1>[CH2:33]([N:18]([CH2:16][CH3:17])[CH2:19][CH2:20][N:21]1[C:31]2[C:26](=[C:27]([Br:32])[CH:28]=[CH:29][CH:30]=2)[C:24]([OH:25])([C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)[C:22]1=[O:23])[CH3:34]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 123250Benzo(b)thiophene, 3-bromo-HCID 10958318HCID 10958318, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18518542HCID 18518542, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3-bromobenzo[b]thiophene (146.5 mg, 2.2 eq) in anhydrous THF (2 mL) at −40° C. (bath temperature) was added t-BuLi (0.40 mL, 1.70 M in pentane, 2.1 eq). The resulting light yellow coloured solution was stirred for 30 minutes, after which 1-(2-diethylaminoethyl)-4-bromoisatin (100.0 mg, 3.08×10−4 mol) in anhydrous THF (2 mL) was added. Stirring was continued at −40° C. for 9 hours. Saturated aqueous NH4Cl (1.5 mL) was added and the mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration, the solvent was removed in vacuo. Purification was carried out by column chromatography (silica gel, eluting 1%-2% MeOH in CHCl3) to give the title compound as a yellow/brown powder (119.3 mg, 84%).

Workup

  1. stirringStirring
  2. waitwas continued at −40° C. for 9 hours
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined extracts were dried (anhydrous Na2SO4)
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customPurification
  8. washwas carried out by column chromatography (silica gel, eluting 1%-2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-cd26d256797341d381a415a13342bcb7
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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