2-(Tributylstannyl)pyridine → HCID 11650493, compound

HRID 1158521Notes

Reaction equation

HRID 1158521 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].CCCC[Sn]([C:59]1[N:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)(CCCC)CCCC>>[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:63]2[CH:62]=[CH:61][CH:60]=[CH:59][N:64]=2)=[CH:40][CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 11513133HCID 11513133, compound

Product 1

HCID 11650493HCID 11650493, compound

Procedure

The title compound was prepared according to Method A, using compound 19 (100 mg, 0.147 mmol), 2-(1,1,1-tributylstannyl)pyridine (220 mg, 0.598 mmol), Pd(PPh)3Cl2 (5.12 mg, 0.0072 mmol) and CuO (11.7 mg, 0.147 mmol). Purification by RP-LC-MS (40 min gradient of 10-100% CH3CN in 0.05% aqueous formic acid) gave the product (17.2 mg, 17%) as a white solid.

Workup

  1. customPurification by RP-LC-MS (40 min gradient of 10-100% CH3CN in 0.05% aqueous formic acid)

Sources & evidence

ORD record
ord-31fe751f00d64b298de7f9080d46f215
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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