Cesium carbonate → HCID 59352676, compound

HRID 1407734Notes

Reaction equation

HRID 1407734 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:13]3=[CH:14][C:15]4[O:19][CH2:18][O:17][C:16]=4[CH:20]=[C:12]3[O:11][CH2:10]2)[C:2]1=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:28][C:29]1[S:33][N:32]=[C:31]([CH2:34]Cl)[N:30]=1>CC(C)=O.CC(=O)CC>[Cl:28][C:29]1[S:33][N:32]=[C:31]([CH2:34][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]3([C:13]4=[CH:14][C:15]5[O:19][CH2:18][O:17][C:16]=5[CH:20]=[C:12]4[O:11][CH2:10]3)[C:2]2=[O:21])[N:30]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazoleHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 59352676HCID 59352676, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a stirred solution of spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (1.33 g, 4.73 mmol) in acetone (50 mL) and 2-butanone (10 mL) were added cesium carbonate (3.10 g, 9.46 mmol) and 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole (1.00 g, 5.92 mmol). The reaction was stirred at ambient temperature for 16 h, then filtered and concentrated in vacuo to dryness. The residue was purified by flash chromatography with ethyl acetate in hexanes (15% to 50% gradient) to afford 1′-[(5-chloro-1,2,4-thiadiazol-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.43 g, 22%) as a colorless solid: mp 114-116° C.; 1H NMR (300 MHz, DMSO-d6) δ7.29 (dd, J=7.7, 7.7 Hz, 1H), 7.21 (d, J=7.0 Hz, 1H), 7.08-7.03 (m, 2H), 6.71 (s, 1H), 6.32 (s, 1H), 5.93 (d, J=3.0 Hz, 2H), 5.24 (ABq, 2H), 4.78 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ 177.2, 174.2, 170.6, 155.7, 148.8, 142.4, 142.2, 132.2, 129.3, 124.1, 123.7, 120.4, 109.8, 103.5, 101.9, 93.8, 79.9, 57.9, 41.6; MS (ES+) m/z 414.1 (M+1), 416.1 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo to dryness
  3. customThe residue was purified by flash chromatography with ethyl acetate in hexanes (15% to 50% gradient)

Sources & evidence

ORD record
ord-b8f26ec4de004e5684f77e14666f8bd1
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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