2-Bromopyridine → HCID 86630255, compound

HRID 422517Notes

Reaction equation

HRID 422517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([C:16](=[O:21])[CH2:17][CH2:18][C:19]#[CH:20])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([C:16](=[O:21])[CH2:17][CH2:18][C:19]#[C:20][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:5]=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([C:16](=[O:21])[CH2:17][CH2:18][C:19]#[CH:20])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 86630255HCID 86630255, compound

Product 2

HCID 66598021HCID 66598021, compoundHCID 86630255HCID 86630255, compoundYield 179.1%

Procedure

The title compound was prepared in accordance with the general method of Example 244(C), from tert-butyl 3-chlorophenyl(pent-4-ynoyl)carbamate (250 mg, 0.82 mmol) and 2-bromopyridine (129 mg, 0.82 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column cyclohexane/AcOEt 70/30 as eluent) to afford 226 mg of tert-butyl 3-chlorophenyl(pent-4-ynoyl)carbamate as a brown oil (Yield: 72%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column cyclohexane/AcOEt 70/30 as eluent)

Sources & evidence

ORD record
ord-de0a20615e324b179f712292d13d5e68
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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