2-Bromopyridine → HCID 66674141, compound

HRID 422431Notes

Reaction equation

HRID 422431 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:12][C:13](=[O:28])[N:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[C:15](=[O:20])[CH2:16][CH2:17][C:18]#[CH:19])([CH3:11])([CH3:10])[CH3:9]>>[C:8]([O:12][C:13](=[O:28])[N:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[C:15](=[O:20])[CH2:16][CH2:17][C:18]#[C:19][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:11])([CH3:9])[CH3:10].[C:8]([O:12][C:13](=[O:28])[N:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[C:15](=[O:20])[C:16]#[C:17][CH2:18][CH2:19][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 86630251HCID 86630251, compound

Product 2

HCID 66598417HCID 66598417, compoundHCID 66674141HCID 66674141, compoundYield 120.9%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-pyridine (137 mg, 0.86 mmol) and (3-fluoro-phenyl)-pent-4-ynoyl-carbamic acid tert-butyl ester (250 mg, 0.86 mmol). Reaction time: 3 hours. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 190 mg (0.52 mmol, 60%) of (3-fluoro-phenyl)-(5-pyridin-2-yl-pent-ynoyl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-afc7f7c7daa54669aaa84a1cc47b8161
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

Loading…