HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethyl Acetate → HCID 89726251, compound

HRID 1777762
Notes
Print preview

Reaction equation

HRID 1777762 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=1.CC1(C)C(C)(C)OB([C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)O1.CC(=O)OCC>O1CCOCC1.C([O-])([O-])=O.[K+].[K+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:28]([O:27][C:25]([N:22]1[CH2:21][CH:20]=[C:19]([C:2]2[CH:3]=[N:4][N:5]([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=2)[CH2:24][CH2:23]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 17024755(4-Bromo-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 89726251HCID 89726251, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 11430Potassium CarbonateSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-bromo-1H-pyrazol-1-yl)acetic acid (867 mg), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.2 g) and Pd(PPh3)4 (232 mg) in dioxane (15 mL) and sat. K2CO3 (7.5 mL) was heated at 100° C. overnight. After cooling down, EA was added and the mixture was washed with water and brine. The combined aq. layers were acidified to pH=2 with NaHSO4 and extracted with EA. The org. layers from the second extraction were dried (MgSO4), filtered off and evaporated in vacuo to afford 1.05 g of brown resin that was used without purification. LC-MS (B): tR=0.72 min; [M+H]+: 308.26.

Workup

  1. temperatureAfter cooling down
  2. washthe mixture was washed with water and brine
  3. extractionextracted with EA
  4. extractionlayers from the second extraction
  5. dry with materialwere dried (MgSO4)
  6. filtrationfiltered off
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6a98f47c8d31451ba19bca4b0b4ae57c
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266876B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes