Tetrabutylammonium Fluoride → HCID 118093713, compound

HRID 625704Notes

Reaction equation

HRID 625704 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[C:15]2[C:10](=[C:11]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[C:12]([C:16]#[N:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:25][C:22]1[N:21]=[CH:20][C:19]([CH2:18][C:11]2[C:12]([C:16]#[N:17])=[CH:13][CH:14]=[C:15]3[C:10]=2[CH2:9][CH2:8][C@@H:7]3[OH:6])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123855249HCID 123855249, compound

Product 1

HCID 118093713HCID 118093713, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(6-chloro-pyridin-3-ylmethyl)-indan-5-carbonitrile (130 mg, 0.33 mmol) is suspended in dry tetrahydrofuran (5 mL) and cooled in an ice bath. Tetrabutylammonium fluoride (1 M in tetrahydrofuran, 0.65 mL, 0.65 mmol) is added, the mixture allowed to warm to room temperature and stirred for 3 hours. The mixture is concentrated under vacuum, diluted with ethyl acetate and washed with saturated ammonium chloride solution. The organic phase is evaporated to give crude title compound which is used directly in the next step (Yield 143 mg). LC (METHOD 6): tR=0.47 min; Mass spectrum (ES+): m/z=285 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe mixture is concentrated under vacuum
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated ammonium chloride solution
  5. customThe organic phase is evaporated

Sources & evidence

ORD record
ord-bb692f495fb34bd2a70d4d943d62ac36
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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