Methanol → HCID 19104978, compound

HRID 1197790Notes

Reaction equation

HRID 1197790 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1.CO.Cl.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][Cl:35])[CH:29]=1>O.[OH-].[Na+]>[ClH:1].[ClH:35].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([CH2:34][C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=3)([CH2:17][C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 19104983HCID 19104983, compound

Product 1

HCID 19104978HCID 19104978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A mixture of 1,3-dihydro-1-(4-chlorophenyl)-3-(4-pyridinylmethyl)-2H-pyrrolo[2,3-b]pyridin-2-one (3.0 g, 8.93 mmol) and 20 ml 1N NaOH was treated with enough MeOH to effect solution. The mixture was treated dropwise with 3-picolyl chloride hydrochloride (1.6 g, 9.82 mmol) in 10 ml water. The mixture was stirred at room temperature for 2 h, and treated with an additional 20 ml IN NaOH. The mixture was stirred at room temperature for 24 h and concentrated in vacuo. The residue was partitioned between 200 ml CH2Cl2, washed with brine, dried over MgSO4, filtered, and treated with 20 ml 1N HCl/Et2O. The resulting precipitate was collected by filtration, washed with ether, and dried to give the desired product in 90% (4.0 g) yield; mp 208°-211° C., dec.; IR(nujol): 1720 cm-1 (CO); 1H NMR(DMSOd6TMS): d 3.65 [m, 2H, CH2 -(3-Pyr)], 3.71-3.91 [q, 2H, CH2 -(4-Pyr)], [7.06 (d, 2H), 7.22 (m, 1H), 7.53 (d, 2H), 7.60 (d, 2H), 7.85 (dd, 1H), 8.04 (dd, 2H), 8.22 (d, 1H), 8.52 (s, 1H), 8.84 (d, 3H), Ar]; mass spec m/e 427 (M+1).

Workup

  1. stirringThe mixture was stirred at room temperature for 24 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 200 ml CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. additiontreated with 20 ml 1N HCl/Et2O
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-40da3ddd9a95403db8d6744b4f5058f3
Source dataset
uspto-grants-1994_01
Patent number
US05278162

Reaction notes

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