Triethylamine → (4-bromo-3-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

HRID 1908175Notes

Reaction equation

HRID 1908175 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:44][N:45]1[C:49]2[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=3[O:56][C:57]3([CH2:62][CH2:61][NH:60][CH2:59][CH2:58]3)[C:48]=2[CH:47]=[N:46]1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:60]2[CH2:61][CH2:62][C:57]3([C:48]4[CH:47]=[N:46][N:45]([CH3:44])[C:49]=4[C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=4[O:56]3)[CH2:58][CH2:59]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162158674-Bromo-3-methoxybenzoic acidHCID 585507381-Methylspiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]

Product 1

HCID 58551290(4-bromo-3-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 100 mL round bottom flask was added 4-bromo-3-methoxy-benzoic acid (860 mg, 3.7 mmol), HATU (1.4 g, 3.7 mmol), DMF (6 mL) and triethylamine (1.4 mL, 10 mmol). The reaction mixture was allowed to stir for 10 minutes. 1-Methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (860 mg, 3.4 mmol) dissolved in DMF (6 mL) was added, and the mixture was allowed to stir at 25° C. After 2 h, the reaction was quenched with brine and was extracted with ethyl acetate. The combined organic layers were washed with brine 3 times. The combined organic layer were dried over sodium sulfate and evaporated. The residue was purified via silica gel chromatography (5-90% EtOAc:hexanes) to give (4-bromo-3-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone as white foam. ESI-MS m/z calc. 467.1. found 468.2 (M+1)+. Retention time: 3.04 minutes (4 min run).

Workup

  1. additionwas added
  2. stirringto stir at 25° C
  3. waitAfter 2 h
  4. customthe reaction was quenched with brine
  5. extractionwas extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine 3 times
  7. dry with materialThe combined organic layer were dried over sodium sulfate
  8. customevaporated
  9. customThe residue was purified via silica gel chromatography (5-90% EtOAc:hexanes)

Sources & evidence

ORD record
ord-f53d8fdc8dc040f08e7606a2227e33ed
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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