Water → HCID 57494746, compound

HRID 861160Notes

Reaction equation

HRID 861160 reaction equation
CN(C)[CH:3]=[O:4].[Br:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:22]=[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[N:15]3[N:14]=2)[CH:10]=[CH:11][CH:12]=1.P(Cl)(Cl)(Cl)=O.O>ClCCl>[Br:6][C:7]1[CH:8]=[C:9]([C:13]2[C:22]([CH:3]=[O:4])=[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[N:15]3[N:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 573500612-(3-Bromophenyl)-7-chloropyrazolo[1,5-a]pyridine

Product 1

HCID 57494746HCID 57494746, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-Dimethylformamide (150 mL) and 2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine (10.3 g, 33 mmol) was cooled to 0° C. and treated with phosphorous oxychloride (4.7 mL, 50 mmol). After the addition was complete, the mixture was warmed to room temperature and the resultant solution was stirred over the weekend. Water was added, followed by dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was washed with diethyl ether and hexanes to give 2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine-3-carbaldehyde (10.6 g, 96%) as a fluffy white solid. 1H NMR (DMSO-d6): δ 10.09 (s, 1 H), 8.37 (d, 1 H), 8.11 (d, 1H), 7.95 (d, 1H), 7.80 (m, 2 H), 7.65 (d, 1 H), 7.55 (m, 1 H).

Workup

  1. additionAfter the addition
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe residue was washed with diethyl ether and hexanes

Sources & evidence

ORD record
ord-a6af6c0732be48b68270e436007a54f3
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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