Dimethylformamide → HCID 11520444, compound

HRID 1158527Notes

Reaction equation

HRID 1158527 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][C:41](Br)=[CH:40][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.CCN(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][C:41]([C:53]#[C:52][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH:40][CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11513133HCID 11513133, compound

Product 1

HCID 11520444HCID 11520444, compoundYield 22.3%

Reagents, catalysts & solvents 4

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

Procedure

Compound 36 was prepared according to Method D, using compound 19 (88.4 mg, 0.130 mmol), phenylacetylene (0.0285 mL, 0.260 mmol), Et3N (0.181 mL, 1.30 mmol), Pd(PPh3)2Cl2 (4.49 mg, 0.0064 mmol), CuI (2.46 mg, 0.0129 mmol) and DMF (2.1 mL). RP-LC-MS (35 min gradient of 40-100% CH3CN in 0.05% aqueous formic acid) afforded the title compound (20.4 mg, 22%) as a white solid.

Workup

  1. customCompound 36 was prepared

Sources & evidence

ORD record
ord-167a656b5af6420b97a9acd3e5edae1a
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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