Sodium Carbonate → HCID 135423852, compound

HRID 1039432Notes

Reaction equation

HRID 1039432 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=O.C([O:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH:23]1[CH:22]=[CH:21][C:20]2[N:19]=[C:18]([C:7]3[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:10]=4[NH:9][C:8]=3[OH:11])[C:17](=[O:16])[C:25]=2[CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11841Indoxyl acetateHCID 5864187-Fluoroisatin

Product 1

HCID 135423852HCID 135423852, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (25 mL) was vigorously stirred under nitrogen for 20 min and then 7-fluoroisatin (IIIa) (150 mg, 0.91 mmol) and 3-acetoxyindole (106 mg, 0.61 mmol) were added and stirring was Continued for 5 min. Anhydrous Na2CO3 (155 mg) was added and the stirring was continued for 3 h. The dark precipitate was filtered and washed with aqueous methanol (1:1, 20 mL) to give 7 (130 mg, 0.46 mmol, 77%) selectively in a Z form. 1H NMR (DMSO, 400 MHz, δ ppm, J in Hz) 11.37 (1H, s, N′—H), 11.12 (1H, s, N—H), 8.58 (1H, d, J=7.7 Hz, H-4), 7.64 (1H, d, J=7.5 Hz, H-4′), 7.57 (1H, t, J=7.5 Hz H-6′), 7.42 (1H, d, J=7.5 Hz, H-7′), 7.15 (1H, t, J=8.0 Hz, H-5), 7.02 (2H, m, H-5′, 6); CI-MS m/z 281 (M+H)+. Anal. (C16H9N2O2F) C, H, N.

Workup

  1. waitthe stirring was continued for 3 h
  2. filtrationThe dark precipitate was filtered
  3. washwashed with aqueous methanol (1:1, 20 mL)

Sources & evidence

ORD record
ord-9ad96b3c09f449699af52cc284105ec2
Source dataset
uspto-grants-2013_10
Patent number
US08552053B2

Reaction notes

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