3-(Tributylstannyl)pyridine → HCID 68678286, compound

HRID 1158522Notes

Reaction equation

HRID 1158522 reaction equation
[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13](CC1C=CC(Br)=CC=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].CCCC[Sn]([C:59]1[CH:64]=[CH:63][CH:62]=[N:61][CH:60]=1)(CCCC)CCCC>>[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([N:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:59]2[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=2)=[CH:19][CH:18]=1)[NH: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:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:11])[C:6]([CH3:7])([CH3:8])[CH3:9]

Participants

3

Reactant 2

HCID 34838483-(Tributylstannyl)pyridineHCID 11513133HCID 11513133, compound

Product 1

HCID 68678286HCID 68678286, compound

Procedure

The title compound was prepared according to Method A, using compound 19 (90.0 mg, 0.132 mmol), 3-(1,1,1-tributylstannyl)pyridine (194 mg, 0.527 mmol), Pd(PPh)3Cl2 (4.63 mg, 0.0065 mmol) and CuO (10.5 mg, 0.132 mmol). The product (24.0 mg, 27%) was afforded as a white solid after purification by RP-LC-MS (40 min gradient of 10-100% CH3CN in 0.05% aqueous formic acid).

Sources & evidence

ORD record
ord-eed5cc0b71c54e6a8e9739a7f15a6062
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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