Dimethylformamide → HCID 86609780, compound

HRID 1376239Notes

Reaction equation

HRID 1376239 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([Br:29])[CH:24]=1.CN([CH:33]=[O:34])C>CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[Br:29][C:25]1[CH:24]=[CH:23][C:28]([CH2:33][O:34][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:27][N:26]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 86609780HCID 86609780, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

Trityl chloride (3.90 g, 14 mmol), 4-DMAP (2.08 g, 17 mmol) and 2-bromo-5-hydroxymethylpyridine 33 (1.88 g, 10 mmol) (Ellingboe, J. W., et al., J. Med. Chem. 1994, 37, 542–550) were dissolved in DMF (15 mL) and the solution was stirred at 80° C. for 48 hours. A white precipitate formed during this time. After cooling, the mixture was diluted with NaHCO3 (sat., 25 mL) and extracted with EtOAc (3(50 mL). The combined extract was washed with brine, with a few drops of NaOH (1 M) added (2(100 mL). After drying and evaporation, the solid residue was purified by flash chromatography (silica, hexanes:EtOAc 15:1) to yield 34 as a white solid (4.46 g, 100%). TLC Rf=0.30 (silica, hexanes:EtOAc 15:1); IR (film) vmax 3057, 1448, 1086, 764, 700, 632 cm−1; MALDI-FTMS m/z 430.0792 (MH+), calcd for C25H21BrNO 430.0801.

Workup

  1. customA white precipitate formed during this time
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc (3(50 mL)
  4. extractionThe combined extract
  5. washwas washed with brine, with a few drops of NaOH (1 M)
  6. additionadded (2(100 mL)
  7. customAfter drying
  8. customevaporation
  9. customthe solid residue was purified by flash chromatography (silica, hexanes:EtOAc 15:1)

Sources & evidence

ORD record
ord-66d78810b0ee4f79a9df56cb5f73ca83
Source dataset
uspto-grants-2007_01
Patent number
US07169930B2

Reaction notes

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