Pyridine → HCID 66693973, compound

HRID 1469195Notes

Reaction equation

HRID 1469195 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C@H:9]2[C@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:10]2)=[CH:5][C:6]=1[CH2:7]O.P(Br)(Br)[Br:49].N1C=CC=CC=1>CCOCC>[CH2:32]([O:31][C@H:12]1[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:9]([C:4]2[S:3][C:2]([Cl:1])=[C:6]([CH2:7][Br:49])[CH:5]=2)[O:10][C@@H:11]1[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 66693979HCID 66693979, compound

Product 1

HCID 66693973HCID 66693973, compoundYield 193.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of alcohol 37 (3.86 g, 5.75 mmol) in ether (50 mL) were added phosphorus tribromide (0.3 mL, 2.88 mmol) and catalytic amount of pyridine at 0° C. The mixture was allowed to warm to room temperature and stirred at room temperature for 2 hours. The mixture was extracted with EtOAc/H2O (100 mL/150 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to yield the title compound 38 (4.1 g, 97%), which was carried on to the next step without further purification.

Workup

  1. extractionThe mixture was extracted with EtOAc/H2O (100 mL/150 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e296a73a77eb43bb8aeb32de6ea7f361
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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