Dimethylformamide → HCID 11672070, compound

HRID 1158528Notes

Reaction equation

HRID 1158528 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]([C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1)#[CH:47].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:47]#[C:46][C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[CH:40][CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 11513133HCID 11513133, compound

Product 1

HCID 11672070HCID 11672070, compoundYield 45.4%

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 38 was prepared according to Method D, using compound 19 (85.8 mg, 0.126 mmol), 3-(ethynyl)pyridine (0.0260 mL, 0.252 mmol), Et3N (0.176 mL, 1.26 mmol), Pd(PPh3)2Cl2 (4.42 mg, 0.0063 mmol), CuI (2.40 mg, 0.0126 mmol) and DMF (2.1 mL). RP-LC-MS (35 min gradient of 25-100% CH3CN in 0.05% aqueous formic acid) afforded the title compound (40.3 mg, 45%) as a white solid.

Workup

  1. customCompound 38 was prepared

Sources & evidence

ORD record
ord-99f3618036b14dfb98eef936d22debd0
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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