2-Bromopyridine → HCID 66597943, compound

HRID 334714Notes

Reaction equation

HRID 334714 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:12][C:13](=[O:29])[N:14]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[CH3:28])[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:29])[N:14]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[CH3:28])[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)([CH3:10])([CH3:11])[CH3:9]

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 86673179HCID 86673179, compound

Product 1

HCID 66597943HCID 66597943, compoundYield 61%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-pyridine (129 mg, 0.82 mmol) and (4-fluoro-2-methyl-phenyl)-pent-4-ynoyl-carbamic acid tert-butyl ester (250 mg, 0.82 mmol). Reaction time: 3 hours. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 190 mg (0.50 mmol, 61%) of (4-fluoro-2-methyl-phenyl)-(5-pyridin-2-yl-pent-4-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-feeadc07c80343d3b3c192fa3580fa31
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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