Dimethylformamide → HCID 11527707, compound

HRID 1158531Notes

Reaction equation

HRID 1158531 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]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=1)#[CH:47].N(CC)CC.CN(C=O)C>C(O)=O.[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:47]#[C:46][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=2)[CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 137268EthynylpyridineHCID 11693236HCID 11693236, compound

Product 1

HCID 11527707HCID 11527707, compound

Reagents, catalysts & solvents 3

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

Procedure

The title compound was synthesized according to Method C using compound 26 (79.4 mg, 0.117 mmol), 2-(ethynyl)pyridine (15.3 mg, 0.148 mmol), Et2NH (0.105 mL, 1.01 mmol) Pd(PPh3)2Cl2 (6.50 mg, 0.00926 mmol), CuI (1.50 mg, 0.00788 mmol) and DMF (2 mL). RP-LC-MS (35 min gradient of 0-100% CH3CN in 0.05% aqueous formic acid) gave the product (15.9 mg, 19%) as a white solid.

Sources & evidence

ORD record
ord-97d29b87cc08467195d84c0dc8e4cd22
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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