4-Iodotoluene → HCID 15296884, compound

HRID 863833Notes

Reaction equation

[C:1]([N:20]([CH2:27][CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:38][C:39]3[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=3[N:41]=2)=[CH:33][CH:32]=1)[CH2:21][CH2:22][O:23][CH2:24][C:25]#[CH:26])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1>C(N)CCC.[Cu]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:1]([N:20]([CH2:27][CH2:28][O:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[O:38][C:39]3[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=3[N:41]=2)=[CH:35][CH:36]=1)[CH2:21][CH2:22][O:23][CH2:24][C:25]#[C:26][C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(prop-2-ynyloxy)ethanamine (0.517 g; 0.87 mmol), 4-iodotoluene (0.262 g; 1.2 mmol) and copper (I) iodide (3.5 mg; 2%/wt) are dissolved in BuNH2 (4 ml) in an inert atmosphere (argon). To this is added (PPh3)2PdCl2, [bis(triphenylphosphine)palladium chloride], (6 mg; 1%/wt) and the reaction is heated at 75° C. for 1 hour. The mixture is then concentrated in vacuo and purified by column chromatography using 10 Et3N/10 CH2Cl2 /PE to obtain N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-[3-(4-methylphenyl)prop-2-ynyloxy]ethanamine which is used directly in Step G.

Workup

concentrationThe mixture is then concentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-3771ea54b67b48cf82caacc88714b863
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561143

Reaction notes

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