Hydrochloric Acid → HCID 71668229, compound

HRID 508649Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)O[C:5](=O)[C:4]=1[C:17]([O:19][CH3:20])=[O:18].[C:21]1([N:27]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][CH2:32]C3=O)=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[K+].Cl>CN(C=O)C>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:32]3[CH2:31][CH2:30][C:29]4[C:34](=[CH:35][N:27]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:28]=4)[C:5]=3[C:4]([C:17]([O:19][CH3:20])=[O:18])=[C:3]([S:2][CH3:1])[CH:8]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of methyl 4-(methylthio)-2-oxo-6-(4-fluorophenyl)-2H-pyran-3-carboxylate (294 mg, 1 mmol), 2-phenyl-6,7-dihydro-2H-indazol-4(5H)-one (212 mg, 1 mmol) and powdered KOH (84 mg, 1.5 mmol) in dry DMF (5 mL) was stirred at 25° C. for 7 hr. At the end the reaction mixture was poured into ice water with vigorous stirring and finally neutralized with dilute HCl. The solid thus obtained was filtered and purified on a neutral alumina column using 15% chloroform in hexane as eluent to yield 52% of methyl 6-(4-fluorophenyl)-8-(methylthio)-2-phenyl-4,5-dihydro-2H-benzo[e]indazole-9-carboxylate. White solid; mp-182-184° C.; 1H NMR (300 MHz, CDCl3) δ 2.48 (s, 3H, CH3), 2.82-2.90 (m, 4H, 2CH2), 4.01 (s, 3H, OCH3), 7.10-7.19 (m, 3H, ArH), 7.27-7.36 (m, 3H, ArH), 7.42-7.51 (m, 2H, ArH), 7.67 (d, J=7.62 Hz, 2H, ArH), 7.98 (s, 1H, ArH); MS (ESI) m/z 445 (M++1).

Workup

stirringwith vigorous stirring
customThe solid thus obtained
filtrationwas filtered
custompurified on a neutral alumina column

Sources & evidence

ORD record: ord-5a314f2b21f24dcc8497fd82f5b272e0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096539B2

Reaction notes

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