3-Bromopyridine → HCID 25135290, compound

HRID 388423Notes

Reaction equation

HRID 388423 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:24]([CH:25]=[O:26])=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[S:22][N:21]=2)=[CH:16][CH:15]=1>CCOCC.C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:24]([CH:25]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[OH:26])=[C:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:22][N:21]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 122863-BromopyridineHCID 58432985HCID 58432985, compoundHCID 178418339Butyllithium

Product 1

HCID 25135290HCID 25135290, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromopyridine (103 mg) in 2.5 ml of ether is cooled to −78° C. under N2 and to this is added drop-wise a BuLi solution (0.375 ml, 1.6 M in hex). After stirring for 15 min, a solution of 15 (150 mg) in THF is added drop-wise. Stirring is continued for 20 min at −78° C., the red colored reaction mixture is quenched with water (5 ml) and the cooling bath is removed. Water (25 ml) and EtOAc (30 ml) are added. After washing, the layers are separated, the organic layer is washed with brine, dried and concentrated to afford an orange foam (200 mg). The material is purified by flash column chromatography (2% MeOH in CH2Cl2). Desired compound 16 is obtained as white foam showing the expected mass in LCMS (M+1:379 and its isotopes at 380; 381 and 382).

Workup

  1. stirringStirring
  2. waitis continued for 20 min at −78° C.
  3. customthe red colored reaction mixture is quenched with water (5 ml)
  4. customthe cooling bath is removed
  5. additionWater (25 ml) and EtOAc (30 ml) are added
  6. washAfter washing
  7. customthe layers are separated
  8. washthe organic layer is washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b77b7710fa30457f896e3c8a0ce9fe9a
Source dataset
uspto-grants-2013_02
Patent number
US08377953B2

Reaction notes

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