Ethanol → HCID 57476245, compound

HRID 1994868Notes

Reaction equation

HRID 1994868 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[NH:7][C:6]([C:14]1[S:15][CH:16]([CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH2:17][N:18]=1)=[CH:5]2.[Cl-].[Ca+2].[Cl-].C(O)C.O1CCCC1>[Fe].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH2:11])[CH:10]=1)[NH:7][C:6]([C:14]1[S:15][CH:16]([CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[CH2:17][N:18]=1)=[CH:5]2

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 5284359Calcium ChlorideHCID 57476244HCID 57476244, compound

Product 1

HCID 57476245HCID 57476245, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-7-nitro-1H-indole (2.4 g), iron (1.7 g), calcium chloride (310 mg), ethanol (50 mL), tetrahydrofuran (25 mL) and water (5 mL) was stirred under heating at 80° C. for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried (MgSO4), and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give the title compound (500 mg, yield 22%) as yellow crystals from a fraction eluted with ethyl acetate:hexane=50:50. MS: 396 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19c7aec4b1134d4589ded0487a465a39
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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