Dimethylformamide → HCID 11707444, compound

HRID 1158530Notes

Reaction equation

HRID 1158530 reaction equation
[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40](Br)[CH:39]=1)[CH2:14][C@:15]([OH:36])([C:23](=[O:35])[NH:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7].[C:46]1([C:52]#[CH:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.N(CC)CC.CN(C=O)C>C(O)=O.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.[Cu]I.CC#N>[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([CH2:14][C@:15]([OH:36])([C:23](=[O:35])[NH:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:53]#[C:52][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 10821PhenylacetyleneHCID 11693236HCID 11693236, compound

Product 1

HCID 11707444HCID 11707444, compoundYield 27.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 284Formic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Method C was followed using compound 26 (79.2 mg, 0.116 mmol), phenylacetylene (0.0150 mL, 0.139 mmol), Et2NH (0.110 mL, 1.01 mmol), Pd(PPh3)2Cl2 (6.10 g, 0.00869 mmol), CuI (1.90 mg, 0.00998 mmol) and DMF (2 mL). RP-LC-MS (35 min gradient of 20-90% CH3CN in 0.05% aqueous formic acid) afforded the title compound (22.2 mg, 27%) as a white solid.

Sources & evidence

ORD record
ord-37d2b383f2e942fc92100ce6603538fa
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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