Potassium Carbonate → (4-Cyclopropyl-3-methoxy-phenyl)-(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

HRID 2204270Notes

Reaction equation

HRID 2204270 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3([C:27]4[CH:26]=[N:25][N:24]([CH3:28])[C:23]=4[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:16]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[O:29][CH3:30].[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:31]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][C:13]4([C:27]5[CH:26]=[N:25][N:24]([CH3:28])[C:23]=5[C:22]5[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=5[O:16]4)[CH2:12][CH2:11]3)=[O:9])=[CH:4][C:3]=2[O:29][CH3:30])[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 58551290(4-bromo-3-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

Product 1

HCID 58551382(4-Cyclopropyl-3-methoxy-phenyl)-(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial was added (4-bromo-3-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (70 mg, 0.15 mmol), cyclopropylboronic acid (26 mg, 0.30 mmol), Fibre cat (49 mg, 0.0075 mmol), DMF (0.7 mL), and K2CO3 (150 μL of 3.0 M, 0.45 mmol). The vial was purged with nitrogen and was heated at 120° C. for 2 hours. The reaction was filtered and purified by HPLC (20-99%) MeOH:H2O. ESI-MS m/z calc. 429.2, found 430.4 (M+1)+. Retention time: 2.95 minutes (4 min run).

Workup

  1. customThe vial was purged with nitrogen
  2. filtrationThe reaction was filtered
  3. custompurified by HPLC (20-99%) MeOH
  4. customRetention time: 2.95 minutes (4 min run)

Sources & evidence

ORD record
ord-14ea88e80ad04df9b18de3c9f47daf58
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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