Dichloromethane → HCID 53695021, compound

HRID 1789886Notes

Reaction equation

HRID 1789886 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:13](C=C)=[CH:12][C:11](CO)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]([Br:42])(Br)(Br)Br.C(Cl)[Cl:44]>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:13]([Cl:44])=[CH:12][C:11]([CH2:38][Br:42])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69650328HCID 69650328, compound

Product 1

HCID 53695021HCID 53695021, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of (5-hydroxymethyl-3-vinyl-pyridin-2-yl)carbamic acid tert-butyl ester (10.0 g, 40.0 mmol) in CH2Cl2 (150 ml) and THF (60 ml) was added triphenylphosphine (11.5 g, 44.0 mmol) followed by carbontetrabromide (19.9 g, 60.0 mmol) at 0° C. The mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. Acetonitrile (100 ml) was added and the mixture was kept at −20° C. overnight. The mixture was then filtered and the crystalline residue washed with cold acetonitrile. The product was purified by flash-chromatography (1% MeOH in dichloromethane) to give (5-bromomethyl-3-chloro-pyridin-2-yl)-carbamic acid tert-butyl ester (4.5 g, 36%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionAcetonitrile (100 ml) was added
  3. waitthe mixture was kept at −20° C. overnight
  4. filtrationThe mixture was then filtered
  5. washthe crystalline residue washed with cold acetonitrile
  6. customThe product was purified by flash-chromatography (1% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-0b809378ed0345879f1bed7055ae6671
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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