Carbon tetrabromide → HCID 59299959, compound

HRID 2236549Notes

Reaction equation

HRID 2236549 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.[N-:45]=[N+:46]=[N-:47].[Na+]>O.CN(C)C=O>[N:45]([CH2:15][C:13]1[N:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]([O:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=1)=[N+:46]=[N-:47]

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 59300229HCID 59300229, compound

Product 1

HCID 59299959HCID 59299959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (6-benzyloxy-5-propoxy-pyridin-2-yl)-methanol (1.09 g, 4.0 mmole) and 20 mL of N,N-dimethylformamide stirred and cooled with an ice bath to 0° C. is added triphenylphosphine (1.57 g, 6.0 mmole) followed by carbon tetrabromide (1.99 g, 6.0 mmole). This is stirred for 15 minutes maintaining temperature between 0-5°. Sodium azide is then added (781 mg, 12.0 mmole) and the reaction mixture stirred for 24 hrs at ambient temperature. The reaction mixture is diluted with water and extracted with ether. The combined extracts were dried over sodium sulfate, filtered, evaporated and the residue chromatographed on silica gel eluting with hexane/ethyl acetate to give a-clear liquid, 1.05 g, (88%); MS (ES+): m/z 299.1 (M+H).

Workup

  1. stirringThis is stirred for 15 minutes
  2. temperaturemaintaining temperature between 0-5°
  3. stirringthe reaction mixture stirred for 24 hrs at ambient temperature
  4. extractionextracted with ether
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue chromatographed on silica gel eluting with hexane/ethyl acetate
  9. customto give a-clear liquid, 1.05 g, (88%)

Sources & evidence

ORD record
ord-864ea4f8fcad4607981925cfd28b20cf
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…