Triethylamine → HCID 21090408, compound

HRID 350848Notes

Reaction equation

HRID 350848 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].CC1C=CC(S(O)(=O)=O)=CC=1.[F:17][C:18]1([F:25])[CH2:22][NH:21][C@H:20]([C:23]#[N:24])[CH2:19]1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][CH2:2][C:3]([N:21]1[CH2:22][C:18]([F:25])([F:17])[CH2:19][C@H:20]1[C:23]#[N:24])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 86595241HCID 86595241, compound

Product 1

HCID 21090408HCID 21090408, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a CH2Cl2 solution (5 mL) containing bromoacetyl bromide (365 mg, 1.80 mmol) cooled to −10° C. was added dropwise (2S)-4,4-difluoro2-pyrrolidinecarbonitrile 4-methylbenzenesulfonate (described earlier) (500 mg, 1.64 mmol) and triethylamine (199 mg, 1.97 mmol) in CH2Cl2 (5 mL). After stirring for 2 hours at 10° C. the reaction was quenched with H2O and the organics extracted with CH2Cl2 and washed with 1.0 M HCl. After drying over MgSO4 the solvents were reduced in vacuo yielding 400 mg (1.57 mmol, 96% yield) of the title compound as a yellow oil.

Workup

  1. customwas quenched with H2O
  2. extractionthe organics extracted with CH2Cl2
  3. washwashed with 1.0 M HCl
  4. dry with materialAfter drying over MgSO4 the solvents

Sources & evidence

ORD record
ord-5fca999f17bd4a0f93c25360f72b7073
Source dataset
uspto-grants-2007_02
Patent number
US07183290B2

Reaction notes

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