Ethyl Bromide → HCID 86692147, compound

HRID 527924Notes

Reaction equation

HRID 527924 reaction equation
[CH3:1][Si:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([N:16]3[CH2:20][CH2:19][C@@H:18]([NH:21][C:22]4[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][N:23]=4)[CH2:17]3)[C:10]=2[CH:9]=[CH:8]1.[H-].[Na+].Br[CH2:35][CH3:36]>CN(C=O)C>[CH2:35]([N:21]([C@@H:18]1[CH2:19][CH2:20][N:16]([C:15]2[C:10]3[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:31])([CH3:30])[CH3:1])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:17]1)[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][N:23]=1)[CH3:36]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 86692136HCID 86692136, compound

Product 1

HCID 86692147HCID 86692147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-6-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-ylamino)nicotinonitrile (200 mg, 0.46 mmol) in DMF (5.0 mL) was added NaH (55 mg, 2.3 mmol) in portions at 0° C. The reaction mixture was stirred at ambient temperature for 30 minutes, bromoethane (60 mg, 0.55 mmol) was then added dropwise and the reaction mixture was stirred at ambient temperature for additional 30 minutes. The reaction mixture was quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give the title compound. MS (m/z): 464 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for additional 30 minutes
  2. customThe reaction mixture was quenched with saturated NH4Cl (10 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-b027e3668c6f43ec869327d677c594e2
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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