2-Bromo-3-pyridinol → HCID 15171881, compound

HRID 256860Notes

Reaction equation

HRID 256860 reaction equation
[C:1]([C:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].Br[C:19]1[C:24]([OH:25])=[CH:23][CH:22]=[CH:21][N:20]=1>C(N(CC)CC)C>[O:25]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:2]=[C:1]1[C:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1

Participants

4

Reactant 2

HCID 230702-Bromo-3-pyridinolHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol

Product 1

HCID 15171881HCID 15171881, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This compound was prepared by reacting rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with 2-bromo-3-hydroxypyridine under the conditions described in Example 26, but using twice as much triethylamine and lengthening the reaction time to 3 days. Chromatography of the crude product over the 40-fold amount of silica gel using 10% (V/V) of ethyl acetate in methylene chloride followed by crystallization from ether/hexane and recrystallization from ethyl acetate/hexane gave off-white crystals with m.p. 168°-169°.

Workup

  1. customThis compound was prepared
  2. customto 3 days
  3. customChromatography of the crude product over the 40-fold amount of silica gel using 10% (V/V) of ethyl acetate in methylene chloride followed by crystallization from ether/hexane and recrystallization from ethyl acetate/hexane
  4. customgave off-white crystals with m.p. 168°-169°

Sources & evidence

ORD record
ord-066e3c7255f948169203a77cfb24a679
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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