Diisopropylamine → HCID 86633516, compound

HRID 2428065Notes

Reaction equation

HRID 2428065 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:23])[CH:11]=2)[CH:5]=[C:6](Br)[CH:7]=1.[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)#[CH:25].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.[CH:51]([NH:54]C(C)C)(C)C>O1CCCC1.[Cu]I>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:24]#[C:25][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:23])[CH:11]=2)[CH:5]=[C:6]([C:45]#[C:50][C:49]2[CH:48]=[CH:47][CH:46]=[CH:51][N:54]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 8078CyclohexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 137268EthynylpyridineHCID 86633517HCID 86633517, compound

Product 1

HCID 86633516HCID 86633516, compound

Reagents, catalysts & solvents 2

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

Procedure

In nitrogen atmosphere, ethyl [4-(3,5-dibromophenylsulfanyl)-2-methylphenoxy]-acetate (138 mg, 0.30 mmol; prepared as described in example 1) and 2-ethynylpyridine (80 μL, 0.80 mmol) were dissolved in anhydrous tetrahydrofuran (4 mL). 0.15 M Solution of tri-tert-butylphosphine in cyclohexane (0.2 mL, 0.03 mmol) was added via syringe. Copper(I) iodide (1.9 mg, 0.01 mmol), dichloro(bisbenzonitrile)palladium (5.7 mg, 0.015 mmol) and diisopropylamine (112 μL, 0.80 mmol) were added. Traces of the air were removed and mixture was stirred under nitrogen at ambient temperature overnight and then at 50° C. for 1 h. The mixture was diluted with ethyl acetate (10 mL) and filtered through a short path of silica gel. The filtrate was concentrated and purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3-1:1-3:7) yielding ethyl [4-[3,5-bis-[(pyridin-2-yl)ethynyl]-phenylsulfanyl]-2-methylphenoxy]acetate.

Workup

  1. customTraces of the air were removed
  2. waitat 50° C. for 1 h
  3. additionThe mixture was diluted with ethyl acetate (10 mL)
  4. filtrationfiltered through a short path of silica gel
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3-1:1-3:7)

Sources & evidence

ORD record
ord-7c5319605569433eb2e4d6f6638a9750
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

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