Water → HCID 58565374, compound

HRID 2175353Notes

Reaction equation

HRID 2175353 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=[C:9]2[CH:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])[CH:5]=[CH:6][CH:7]=1.[B-](F)(F)(F)[F:28].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(#N)C.O>>[F:28][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:9]=1[CH:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18]

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 2724933SelectfluorHCID 58565365HCID 58565365, compound

Product 1

HCID 58565374HCID 58565374, compoundYield 15.3%

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl {1-[1-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]ethyl}carbamate (0.10 g, 0.28 mmol) and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (0.10 g, 0.28 mmol) in acetonitrile (1.5 mL, 29 mmol) and water (0.15 mL, 8.3 mmol) was heated at 50° C. overnight. The reaction was cooled and extracted with dichloromethane. The combined organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0-20% EtOAc/hexane) to give the desired product (16 mg, 15%). LCMS calculated for C20H22F2N3O2(M+H)+: m/z=374.2. Found: 374.1.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-392e747130944079b906eba992c0f4dd
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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