1-Ethynyl-3-fluorobenzene → HCID 9837457, compound

HRID 1271558Notes

Reaction equation

HRID 1271558 reaction equation
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)#[CH:11]>C(N(CC)CC)C.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:18][C:14]1[CH:13]=[C:12]([C:10]#[C:11][C:2]2[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 5202181-Ethynyl-3-fluorobenzeneHCID 144180512-Bromo-6-methylpyridin-3-amine

Product 1

HCID 9837457HCID 9837457, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Following the same procedure as described in Example 1, (2-bromo-6-methyl-pyridin-3-yl)amine (200 mg, 1.07 mmol) reacted with (PPh3)2PdCl2 (36 mg, 0.05 mmol), Cul (10 mg, 0.05 mmol) and 1-ethynyl-3-fluorobenzene (148 μl, 1.28 mmol) in triethylamine (5 ml). The crude residue was purified by flash chromatography (hexane/ethyl acetate 4:1) to yield 145 mg (0.64 mmol, 60%) of (2-(3-fluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine as a pale yellow solid. The hydrochloride of (2-(3-fluoro-phenylethynyl)-6-methyl-pyridin-3-yl)amine was prepared as described in Example 1 to yield 148 mg (0.56 mmol, 88%) of the title hydrochloride as a yellow solid.

Workup

  1. customThe crude residue was purified by flash chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-096814c4a2174567922cbfdd113698d9
Source dataset
uspto-grants-2007_04
Patent number
US07205411B2

Reaction notes

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