Diisopropylethylamine → HCID 18672418, compound

HRID 1058239Notes

Reaction equation

HRID 1058239 reaction equation
CCN(C(C)C)C(C)C.Cl.[F:11][C:12]1([F:16])[CH2:15][NH:14][CH2:13]1.Br[CH2:18][C:19]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:20]=1[C:21]#[N:22]>C(Cl)Cl>[Cl:27][C:24]1[CH:25]=[CH:26][C:19]([CH2:18][N:14]2[CH2:15][C:12]([F:16])([F:11])[CH2:13]2)=[C:20]([CH:23]=1)[C:21]#[N:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 126680522-(Bromomethyl)-5-chlorobenzonitrile

Product 1

HCID 18672418HCID 18672418, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA (0.196 mL, 1.12 mmol) was added to a stirred mixture of 3,3-difluoroazetidine hydrochloride (64.8 mg, 0.50 mmol) and 2-bromomethyl-5-chlorobenzonitrile (121.0 mg, 0.52 mmol) in CH2Cl2 (7 mL). After 16 h the reaction was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The residue was partitioned between 1N HCl and ether. The aqueous layer was made neutral with NaHCO3 and was extracted with CH2Cl2. The organic layer was dried with Na2SO4 and then evaporated to give 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile (67.8 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 3.68 (t, J=11.9 Hz. 4H), 3.93 (s, 2H), 7.54 (m, 2H), 7.63 (d, J=2.2 Hz, 1H).

Workup

  1. customAfter 16 h the reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was partitioned between 1N HCl and ether
  6. extractionwas extracted with CH2Cl2
  7. dry with materialThe organic layer was dried with Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-66db6927a39e435687a3f4545f42d76d
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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