Diethyl Ether → HCID 18446618, compound

HRID 1269059Notes

Reaction equation

HRID 1269059 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.[Cl-].[NH4+].CCOCC>O1CCCC1>[Br:16][C:10]1[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[N:8][N:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=12

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 67184N-bromobutanimideHCID 18446629HCID 18446629, compound

Product 1

HCID 18446618HCID 18446618, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Chloro-2-(2-furyl)-pyrazolo[1,5-a]pyridine (0.23 g, 1.05 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled to 0° C. N-Bromosuccinimide (0.19 g, 1.05 mmol) was added. The reaction was stirred for 1 hour. The reaction solution was poured into equal volumes (10 mL) of saturated aqueous ammonium chloride and ether. The ether layer was collected and the solvent removed in vacuo to give the crude product The product was purified by silica gel chromatography (6:1 hexane:ethyl acetate) to give 0.3 g (96%) of 3-bromo-7-chloro-2-(2-furyl)pyrazolo[1,5-a]pyridine as a solid. 1H NMR (CDCl3) δ 7.63 (d, 1H), 7.51 (d, 1H), 7.29 (d, 1H), 7.21 (dd, 1H), 6.98 (d, 1H), 6.58 (dd, 1H); MS m/z 298 (M+1).

Workup

  1. customThe ether layer was collected
  2. customthe solvent removed in vacuo
  3. customto give the crude product The product
  4. customwas purified by silica gel chromatography (6:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-a1d547be1f7c4f23ad469be6a9de4c61
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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