Hydrochloric Acid → HCID 69659177, compound

HRID 1829080Notes

Reaction equation

HRID 1829080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[N:28]1([CH2:34][CH2:35][O:36][C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[C:42](=O)[O:41][CH2:40]3)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.Cl.[OH-].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[C:42]1[C:43]2[C:39](=[CH:38][C:37]([O:36][CH2:35][CH2:34][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:45][CH:44]=2)[CH2:40][O:41]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15142865-MethoxyoxindoleHCID 22061464HCID 22061464, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 69659177HCID 69659177, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-methoxyoxindole (197 mg, 1.21 mmol) in anhydrous THF (10 ml) under nitrogen was added 1.0M LiHMDS/THF solution (2.8 ml, 2.8 mmol). The mixture was stirred at room temperature for 10 minutes, and 5-(2-morpholin-4-yl-ethoxy)-3H-isobenzofuran-1-one (200 mg, 0.76 mmol) was added. After stirred at room temperature for 3.0 hours, the mixture was poured into a mixture of THF (5 ml) and 2M HCl aqueous solution (10 ml), and heated at 60° C. for 40 minutes. The mixture was cooled to room temperature, basified with 5M NaOH aqueous solution, and then poured into water (150 ml). The resulting solid was separated, rinsed with water, and dried to give 5-methoxy-3-[5-(2-morpholin-4-yl-ethoxy)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow solid (275 mg, 89%).

Workup

  1. stirringAfter stirred at room temperature for 3.0 hours
  2. temperatureheated at 60° C. for 40 minutes
  3. temperatureThe mixture was cooled to room temperature
  4. customThe resulting solid was separated
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-3380ae86c92a42dbae7a19391560ccd0
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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