Cesium carbonate → HCID 17980600, compound

HRID 915523Notes

Reaction equation

HRID 915523 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][CH2:34][O:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][O:37]1>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:33][CH2:34][O:35][CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][O:37]4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 1355066154-(2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-ol

Product 1

HCID 17980600HCID 17980600, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (376 mg, 1.146 mmol), cesium carbonate (826 mg, 2.54 mmol), and 2-(2-bromoethoxy)tetrahydro-2H-pyran (380 μL, 2.52 mmol) in DMF (5 mL) at 120° C. for 4 hours. Quench the reaction with saturated sodium chloride and then extract with chloroform. Dry the organic layer over sodium sulfate and concentrate in vacuo. Purify the reaction mixture on a silica gel column eluting with dichloromethane to 10% methanol in dichloromethane to give the desired subtitled intermediate as a yellow oil (424 mg, 81%). MS ES+ m/e 457.0 (M+1).

Workup

  1. customQuench
  2. customthe reaction with saturated sodium chloride
  3. extractionextract with chloroform
  4. dry with materialDry the organic layer over sodium sulfate
  5. concentrationconcentrate in vacuo
  6. customPurify the reaction mixture on a silica gel column
  7. washeluting with dichloromethane to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-10c97d245e2249edabb3753e9f2e6070
Source dataset
uspto-grants-2007_09
Patent number
US07265225B2

Reaction notes

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