Carbonate Ion → HCID 22050690, compound

HRID 1831983Notes

Reaction equation

HRID 1831983 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[C:10]=1[Br:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[N:23][CH:24]=1.C(=O)([O-])[O-]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:18][C:19]2[CH:24]=[N:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:11](=[O:15])[C:10]=1[Br:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 22050212HCID 22050212, compoundHCID 220506385-(Bromomethyl)-2-fluoropyridine

Product 1

HCID 22050690HCID 22050690, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(benzyloxy)-3-bromopyridin-2(1H)-one (0.2 g, 0.00076 mol), 5-bromomethyl-2-fluoropyridine (0.25 g, 0.0013 mol) and pot. Carbonate (0.15 g, 0.0011 mol) in DMF (3.0 ml) was stirred at room temperature for 16 h under argon atmosphere. DMF was distilled in vacuo and the residue was partitioned between water (15 ml) and EtOAc (25 mL). The organic phase was washed with water, dried (Na2SO4) and concentrated under reduced pressure. 1H NMR (CD3OD/400 MHz) δ 8.22 (m, 1H, 2.4 Hz), 7.92 (m, 1H), 7.82 (d, 1H, J=7.6 Hz), 7.44-7.31 (m 5H), 7.03 (m, 1H), 6.49 (d, 1H, J=7.6 Hz), 5.29 (s, 2H), and 5.20 (s, 2H); 19F NMR (CD3OD/400 MHz) δ−72.30 (d, J=6.0 Hz) and −115 (m); ES-HRMS m/z 389.0295 (M+H C18H15N2O2FBr, requires 389.0309).

Workup

  1. distillationDMF was distilled in vacuo
  2. customthe residue was partitioned between water (15 ml) and EtOAc (25 mL)
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f23eb96543594d79bf581c29a21d483c
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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