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Potassium Carbonate → HCID 90416201, compound

HRID 1484786
Notes
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Reaction equation

HRID 1484786 reaction equation
Br[CH2:2][C:3]1[CH2:4][CH2:5][N:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7][C:8]=1[C:9]1[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[CH:11][CH:10]=1.[OH:24][C:25]1[C:30]([CH:31]=[O:32])=[CH:29][C:28]([O:33][CH3:34])=[N:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[CH:31]([C:30]1[CH:29]=[C:28]([O:33][CH3:34])[N:27]=[CH:26][C:25]=1[O:24][CH2:2][C:3]1[CH2:4][CH2:5][N:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7][C:8]=1[C:9]1[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[CH:11][CH:10]=1)=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeHCID 90409261HCID 90409261, compound

Product 1

HCID 90416201HCID 90416201, compoundYield 31.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(bromomethyl)-5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate (18 mg, 0.05 mmol) and 5-hydroxy-2-methoxyisonicotinaldehyde (10 mg, 0.06 mmol) in DMF (1 mL) was added K2CO3 (14 mg, 0.1 mmol). After stirred at room temperature for 1 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=2:1) to give tert-butyl 4-(((4-formyl-6-methoxypyridin-3-yl)oxy)methyl)-3-(1-isopropyl-1H-pyrazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (7.2 mg). 1H NMR (400 MHz, CDCl3) (ppm) 10.39 (s, 1H), 7.79 (s, 1H), 7.56 (d, J=1.6 Hz, 1H), 7.05 (s, 1H), 6.11 (d, J=1.6 Hz, 1H), 4.40 (s, 2H), 4.38 (m, 1H), 4.01 (s, 2H), 3.88 (s, 3H), 3.66 (bs, 2H), 2.46 (bs, 2H), 1.48 (s, 9H), 1.43 (d, 6.4 Hz, 6H). MS (ESI) m/z 457.3 [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=2:1)

Sources & evidence

ORD record
ord-c453c7bae1a04e998f433ebd01b6b074
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