Sodium hydride → HCID 12985914, compound

HRID 1295758Notes

Reaction equation

HRID 1295758 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:12].[CH2:13]([O:15][C:16]([C:18]1[C:19]([O:36][CH3:37])=[C:20]2[N:25]([CH:26]=1)[N:24]=[CH:23][N:22]=[C:21]2NC1C=CC(C)=C(O)C=1)=[O:17])[CH3:14]>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1[C:19]([O:36][CH3:37])=[C:20]2[N:25]([CH:26]=1)[N:24]=[CH:23][N:22]=[C:21]2[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:3][C:4]1=[O:12])=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 321710OxindoleHCID 23589558HCID 23589558, compound

Product 1

HCID 12985914HCID 12985914, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (60%, 44 mg, 1.1 mmol) in THF (1 mL) was added oxindole (133 mg, 1 mmol). The reaction mixture was stirred for 20 min. at rt. Compound G of example 96 (0.1 mmol) was added. The reaction was stirred for 2 hrs at 25° C. The crude material was purified by preparative HPLC followed by chromatography on silica gel eluting with ethyl acetate to provide 5.5 mg (16%) of a yellow solid. MS: [M+H]+=353; 1H NMR (CDCl3): δ 8.42 (s, 0.4H), 8.10 (s, 0.6H), 7.79 (s, 1H), 7.75-6.88 (m, 4H), 4.33 (m, 2H), 3.57 (s, 3H), 1.37 (m, 3H).

Workup

  1. stirringThe reaction was stirred for 2 hrs at 25° C
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-adf7d7476c3c443598409042cf02926d
Source dataset
uspto-grants-2007_07
Patent number
US07244733B2

Reaction notes

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