Triethylamine → HCID 59424500, compound

HRID 500776Notes

Reaction equation

HRID 500776 reaction equation
Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[CH:3]=1.[CH2:22]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[C:23]#[CH:24].C(N(CC)CC)C>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[C:2]([C:24]#[C:23][CH2:22][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[S:10][C:9]=12

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 59424500HCID 59424500, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromide 42 (100 mg, 0.27 mmol) in THF (5 ml) was added 4-(prop-2-ynyl)morpholine (68 mg, 0.54 mmol) [H-W. Tsou, et. al. J. Med. Chem., 2001, 44, 2719-2734], triethylamine (68 mg, 0.67 mmol), CuI (5 mg, 0.03 mmol) and Pd(PPh3)2Cl2 (5.3 mg, 7.56 μmol). The reaction mixture was degassed with nitrogen and refluxed for 2 hrs, cooled to room temperature and adsorbed onto silica. Purification by column chromatography (eluent EtOAc) afforded the title compound 56 as a beige solid (88 mg, 79%). MS (m/z): 397.1 (M+H).

Workup

  1. customThe reaction mixture was degassed with nitrogen
  2. temperaturerefluxed for 2 hrs
  3. customPurification by column chromatography (eluent EtOAc)

Sources & evidence

ORD record
ord-6ed9abcef5994292a70adb993df9599a
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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