1-Butyne → HCID 69514008, compound

HRID 855265Notes

Reaction equation

HRID 855265 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([C:11]#[C:12][CH3:13])[C:5]=1[NH2:14].[CH:16]#CCC.COC(=O)C1C=C(Cl)C=C(I)C=1N>C(N(CC)CC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([C:11]#[C:12][CH2:13][CH3:16])[C:5]=1[NH2:14]

Participants

7

Reactant 3

HCID 78461-ButyneHCID 7020924Methyl 2-amino-5-chloro-3-iodobenzoateHCID 69343046HCID 69343046, compound

Product 1

HCID 69514008HCID 69514008, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

The title compound was synthesized in analogy to 2-amino-5-chloro-3-prop-1-ynylbenzoic acid methyl ester (described in example S85) using 1-butyne (excess ca 3 ml), 2-amino-5-chloro-3-iodo-benzoic acid methyl ester (prepared as described in example S85) (430 mg, 1.38 mmol), copper (I) iodide (19 mg, 0.10 mmol) and bis(triphenyl-phosphine) palladium (II) chloride (71 mg, 0.10 mmol) in triethylamine (10 ml). The final compound was purified by flash column chromatography (9:1 cyclohexane:EtOAc) to give 2-amino-3-but-1-ynyl-5-chlorobenzoic acid methyl ester (120 mg, 37%) as a yellow oil. 1H NMR (CDCl3, 300 MHz): δ 7.76 (d, J=2.5 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 6.37 (br s, 2H), 3.87 (s, 3H), 2.49 (q, J=7.5 Hz, 2H), 1.27 (t, J=7.5 Hz, 3H).

Workup

  1. customThe final compound was purified by flash column chromatography (9:1 cyclohexane:EtOAc)

Sources & evidence

ORD record
ord-ed1ceac0945343b59efa1d6ccd4fc878
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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