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Dimethylformamide → 5-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde

HRID 1484793
Notes
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Reaction equation

HRID 1484793 reaction equation
Br[CH2:2][C:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]=1[C:9]1[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[CH:11][CH:10]=1.[OH:17][C:18]1[C:19](C=O)=[N:20][C:21](C)=[CH:22][CH:23]=1.[C:27]([O-:30])([O-])=O.[K+].[K+].CN([CH:36]=[O:37])C>O.CCOC(C)=O>[CH:14]([N:13]1[C:9]([C:4]2[CH2:5][O:6][CH2:7][CH2:8][C:3]=2[CH2:2][O:17][C:18]2[C:23]([CH:36]=[O:37])=[CH:22][C:21]([O:30][CH3:27])=[N:20][CH:19]=2)=[CH:10][CH:11]=[N:12]1)([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehydeHCID 904080795-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole

Product 1

HCID 863040155-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole (50 mg, 0.19 mmol) (see the synthesis of Compound L) and 3-hydroxy-6-methylpicolinaldehyde (30 mg, 0.24 mmol) in DMF (1 mL) was added K2CO3 (50 mg, 0.38 mmol). After stirred at room temperature for 3 h, it was diluted with water and EtOAc, organic layer was separated, and the aqueous layer was extracted with EtOAc, organic layer was combined, washed with brine, dried and concentrated to give crude product, which was purified by column (Hexanes/EtOAc=40:60) to give 5-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde (37 mg). 1H NMR (400 MHz, CDCl3) δ (ppm) 10.30 (s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.09 (d, J=9.2 Hz, 1H), 6.08 (d, J=2.0 Hz, 1H), 4.42 (m, 1H), 4.38 (s, 2H), 4.18 (s, 2H), 3.98 (t, J=5.6 Hz, 2H), 2.56 (s, 3H), 2.51 (s, 2H), 1.39 (d, J=6.4 Hz, 6H); MS (ESI) m/z 342.4 [M+H]+.

Workup

  1. customwas separated
  2. extractionthe aqueous layer was extracted with EtOAc, organic layer
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by column (Hexanes/EtOAc=40:60)

Sources & evidence

ORD record
ord-665319e5581546b3a773063b437fc1cc
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422279B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes