1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22050609, compound

HRID 1867095Notes

Reaction equation

HRID 1867095 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:12]([O:14][CH3:15])=[O:13])[C:4](=[O:21])[CH:3]=1.N12CCCN=C1CCCCC2.[F:33][C:34]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:35]=1[CH2:36]Br.C([O-])(O)=O.[Na+]>CN(C)C=O>[F:33][C:34]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:35]=1[CH2:36][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:12]([O:14][CH3:15])=[O:13])[C:4](=[O:21])[CH:3]=1

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 516892Sodium BicarbonateHCID 54724199HCID 54724199, compound

Product 1

HCID 22050609HCID 22050609, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 mL round bottomed flask equipped with stirbar and nitrogen inlet was charged with the product of Step 2 (1.6 g, 5.5 mmol) and N,N-dimethyl formamide (10 mL). 1,8-diazabicyclo[5.4.0]undec-7-ene (0.91 mL, 6 mmol) was added followed by 2,4-difluorobenzyl bromide (0.77 mL, 6 mmol). The reaction mixture was stirred at 60 C for 4 h, was poured into saturated aqueous NaHCO3 and was extracted with ethyl acetate. The organic layer was washed with brine, dried with Na2SO4 and concentrated in vacuo to give the title compound as an orange foam (2.13 g, 93%), which was carried on to the next reaction without further purification. 1H NMR (400 MHz, CD3OD) δ 8.17 (dd, J=2.64 and 11.6 Hz, 1H), 7.82 (td, J=2.7 and 6.8 Hz, 1H), 7.57 (m, 1H), 7.29 (d, J=11.6 Hz, 1H), 7.02 (m, 2H), 6.16 (m, 1H), 6.03 (d, J=3.5 Hz, 1H), 5.14 (s, 2H), 3.89 (s, 6H), 1.93 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.43 (1F), −116.04 (1F) ppm. ES-HRMS m/z 416.1310 (M+H calcd for C22H20F2NO5 requires 416.1304).

Workup

  1. customA 100 mL round bottomed flask equipped with stirbar and nitrogen inlet
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-516cfeb3f6324ef9b95ece8a9bcf3813
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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