Toluene → HCID 67263320, compound

HRID 1684927Notes

Reaction equation

HRID 1684927 reaction equation
[NH2:1][C:2]1[C:12](Br)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(C)C=CC=CC=1.O1CCCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I.C(N(CC)CC)C>[NH2:1][C:2]1[C:12]([C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 7210833Ethyl 6-amino-5-bromonicotinate

Product 1

HCID 67263320HCID 67263320, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 6-amino-5-bromonicotinate (245 mg, 1 mmol), phenylacetylene (220 mg, 2.2 mmol), (dppf)PdCl2 (40 mg), CuI (15 mg), toluene (2 mL), tetrahydrofuran (1 mL) and triethylamine (1 mL) was stirred at 80° C. under argon for 2 h. After cooling to RT, the mixture was washed with water, dried and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with ethyl acetate in heptanes (1:1) to provide ethyl 6-amino-5-(2-phenylethynyl)nicotinate (205 mg, 77%) as a solid. LC/MS; (M+H)+=267.2

Workup

  1. temperatureAfter cooling to RT
  2. washthe mixture was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate in heptanes (1:1)

Sources & evidence

ORD record
ord-155f2ab6f82e47c9aa2948d502e9a9bf
Source dataset
uspto-grants-2012_04
Patent number
US08148361B2

Reaction notes

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