Ethyl Acetate → HCID 21467483, compound

HRID 1939307Notes

Reaction equation

C([C:4]1[C:12]2[C:7](=[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]3=[CH:10][CH:11]=2)[N:6]([CH:17]2[CH2:22][CH:21]=[C:20]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:19]=[CH:18]2)[N:5]=1)(O)=O.[C:27](OCC)(=[O:29])C>>[CH3:27][O:29][C:14]1[CH:15]=[CH:16][C:8]2[C:9]([CH:13]=1)=[CH:10][CH:11]=[C:12]1[C:7]=2[N:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:24])=[O:25])=[CH:19][CH:18]=2)[N:5]=[CH:4]1

Participants

Reactant 2

HCID 8857Ethyl Acetate

HCID 57091987HCID 57091987, compound

Product 1

HCID 21467483HCID 21467483, compoundYield 20%

Conditions

Temperature: 295 °C

Procedure

4,5-Dihydro-4- [3-(carboxy)-1H-benz[g]indazol-1-yl]benzenesulfonamide from Step 3 (1.00 g, 2.5 mmol) was placed in a round bottomed flask and heated to 295° C. for 0.5 hour. The residue was dissolved in a small amount of ethyl acetate and purified by flash chromatography, eluting with 40% ethyl acetate in hexane to give 4-[7-methoxy-1H-benz[g]indazol-1-yl]benzenesulfonamide as a white solid (200 mg, 20%): 1H NMR (CD3OD): 8.28 (1H, s), 8.18 (2H, d, J=8.66 Hz), 7.81 (1H, s), 7.77 (2H, d, J=8.66 Hz), 7.59 (1H, d, J=8.86 Hz), 7.52 (1H, d, J=9.27 Hz), 7.46 (1H, d, J=2.62 Hz), 7.0 (1H, dd, J=9.27, 2.62 Hz), 3.91 (3H, s) . Mass spectrum M+H =354. Elemental analysis Calc'd. for C18H15N3O3S: C, 61.18; H, 4.28; N, 11.89; S, 9.07. Found: C, 60.93; H, 4.23; N, 11.73; S, 8.93.

Workup

custompurified by flash chromatography
washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record: ord-8cbd6a90b5b8416b89c59ebfca330a52
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696143

Reaction notes

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