2-Bromo-5-(trifluoromethyl)pyridine → HCID 66762922, compound

HRID 573757Notes

Reaction equation

HRID 573757 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=1.[Si:17]([O:24][C@H:25]1[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]2[N:30]=[C:29]([CH:37]([CH3:39])[CH3:38])[C:28]([CH:40]=[O:41])=[C:27]([I:42])[C:26]1=2)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C1(C)C=CC=CC=1>[Si:17]([O:24][C@H:25]1[CH2:34][C:33]([CH3:35])([CH3:36])[CH2:32][C:31]2[N:30]=[C:29]([CH:37]([CH3:38])[CH3:39])[C:28]([C@H:40]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=3)[OH:41])=[C:27]([I:42])[C:26]1=2)([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 86662512(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 66762922HCID 66762922, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

1.23 ml of a 2.5 M solution of n-butyllithium in toluene are added dropwise to a solution of 695 mg 2-bromo-5-trifluoromethylpyridine in 10 ml toluene at −80° C. The mixture is stirred for 1 hour and then a solution of 600 mg (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde in 1 ml toluene is added dropwise. After stirring the mixture for 1 hour at −80° C. the reaction is quenched by addition of a saturated aqueous ammonium chloride solution. The phases are separated and the aqueous phase is extracted for three times with ethylacetate. The combined organic phases are dried with magnesium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (pentane/diethylether 100:0 to 70:30).

Workup

  1. stirringAfter stirring the mixture for 1 hour at −80° C. the reaction
  2. customis quenched by addition of a saturated aqueous ammonium chloride solution
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted for three times with ethylacetate
  5. dry with materialThe combined organic phases are dried with magnesium sulphate
  6. customthe solvents are evaporated in vacuo
  7. customThe residue is chromatographed on silica gel (pentane/diethylether 100:0 to 70:30)

Sources & evidence

ORD record
ord-f92572120d404bfeb81e65d521c93970
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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