Sodium Hydroxide → tert-butyl 2-(5-chloro-3-(4-hydroxyphthalazin-1-yl)-2-methyl-1H-indol-1-yl)acetate

HRID 750633Notes

Reaction equation

HRID 750633 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[C:10]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](Cl)=[N:20][N:19]=2)=[C:9]1[CH3:29])([CH3:4])([CH3:3])[CH3:2].[OH-:31].[Na+]>CC(O)=O>[C:1]([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[C:10]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:31])[NH:20][N:19]=2)=[C:9]1[CH3:29])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58247160tert-Butyl 2-(5-chloro-3-(4-chlorophthalazin-1-yl)-2-methyl-1H-indol-1-yl)acetate

Product 1

HCID 58247168tert-butyl 2-(5-chloro-3-(4-hydroxyphthalazin-1-yl)-2-methyl-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

The product of step b) (300 mg) was treated with 10 mL HOAc and 2 mL of 1 M NaOH. The suspension was heated to 70° C. for 4 h. The reaction was cooled and partitioned between EtOAc and water. The organic layer was dried over MgSO4 and concentrated to give 300 mg of the sub-title compound as a yellow oil. MS: ESI (negative): 422, 424 (M−H).

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae0c1f4fb04a49aca59fcad20964bda4
Source dataset
uspto-grants-2008_07
Patent number
US07405215B2

Reaction notes

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