Triethylamine → 2-[2-(3-Chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 869333Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]2[NH:23][C:24]([C:26]3[CH:31]=[CH:30][N:29]=[C:28](I)[N:27]=3)=[CH:25][C:19]=2[C:18]1=[O:33])=[O:16])([CH3:13])([CH3:12])[CH3:11].[CH2:34](N(CC)CC)C>C(#N)C.[Cu](I)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>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]2[N:23]([CH3:34])[C:24]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([C:9]#[C:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[N:27]=3)=[CH:25][C:19]=2[C:18]1=[O:33])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

1-Chloro-3-ethynyl-benzene (0.018 g, 0.132 mmol), copper iodide (0.0012 g, 0.006 mmol) and PdCl2(PPh3)2 (0.0023 g, 0.003 mmol) were added under argon to a solution of 2-(2-iodo-pyrimidin-4-yl)-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.030 g, 0.066 mmol) and triethylamine (0.170 ml) in dry ACN (0.500 ml). The reaction mixture was stirred at 80° C. for 3 h in argon atmosphere. The solvent was removed under vacuum and the crude residue was purified by flash chromatography, over silica gel, using DCM/MeOH (9.8:0.2) as eluent, to afford 2-[2-(3-chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-4-oxo-1,4,6,7-tetra-hydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.018 g, 0.04 mmol, 60%).

Workup

customThe solvent was removed under vacuum
customthe crude residue was purified by flash chromatography, over silica gel

Sources & evidence

ORD record: ord-09b2b55dcf9a44c3be6721adc754da73
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969366B2

Reaction notes

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