Isopropyl iodide → (4-ethoxy-2-isopropoxy-phenyl)-(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

HRID 1908180Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][C:15]3([C:29]4[CH:28]=[N:27][N:26]([CH3:30])[C:25]=4[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:18]3)[CH2:14][CH2:13]2)=[O:11])=[C:6]([OH:31])[CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].I[CH:39]([CH3:41])[CH3:40]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:13][CH2:14][C:15]3([C:29]4[CH:28]=[N:27][N:26]([CH3:30])[C:25]=4[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:18]3)[CH2:16][CH2:17]2)=[O:11])=[C:6]([O:31][CH:39]([CH3:41])[CH3:40])[CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a vial containing a solution of (4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (41 mg, 0.1 mmol) in DMF (0.8 mL) was added K2CO3 (69 mg, 0.5 mmol), and 2-iodopropane (15 μL, 0.15 mmol). The mixture was stirred for 3 hours at 25° C. The crude reaction mixture was filtered and purified by HPLC (1-99%) MeOH:H2O to yield (4-ethoxy-2-isopropoxy-phenyl)-(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (17 mg, 33%). ESI-MS m/z calc. 461.5. found 462.2 (M+1)+. Retention time: 3.16 minutes (4 min run). (2-Isopropoxy-4-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone was synthesized using the procedures described above. ESI-MS m/z calc. 447.2. found 448.4 (M+1)+; Retention time: 3.03 minutes (4 min run).

Workup

customThe crude reaction mixture
filtrationwas filtered
custompurified by HPLC (1-99%) MeOH

Sources & evidence

ORD record: ord-194394e260804988b2d9189abccb5c5c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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