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tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate → HCID 66760514, compound

HRID 389451
Notes
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Reaction equation

HRID 389451 reaction equation
[Cl:1][C:2]1[O:12][C:5]2=[C:6]([NH2:11])[N:7]=[CH:8][C:9](I)=[C:4]2[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)[CH:25]=2)O1>COCCOC.O>[C:35]([O:34][C:32]([N:29]1[CH2:28][CH2:27][CH:26]([N:24]2[CH:25]=[C:21]([C:9]3[CH:8]=[N:7][C:6]([NH2:11])=[C:5]4[O:12][C:2]([Cl:1])=[CH:3][C:4]=34)[CH:22]=[N:23]2)[CH2:31][CH2:30]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 45480279tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylateHCID 667601342-Chloro-4-iodofuro[2,3-c]pyridin-7-amine

Product 1

HCID 66760514HCID 66760514, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-Dimethoxyethane
Solvent

Procedure

A mixture of 2-chloro-4-iodofuro[2,3-c]pyridin-7-amine (7.7 g, 26.2 mmol) and tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (10.52 g, 27.7 mmol) in 1,2-dimethoxyethane (300 mL) and water (100 mL) was sparged with N2 for 15 min, then treated with K2CO3 and Pd(PPh3)4. After sparging again with N2 for 5 min, the mixture was heated at reflux 4-6 h. The 1,2-dimethoxyethane was removed in vacuo, water was added and the mixture extracted with DCM. The combined DCM extracts were dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography using triethylamine-coated silica (2% MeOH:DCM) to afford 10 g (80%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.44-1.55 (m, 9H) 1.90-2.12 (m, 2H) 2.21 (d, J=10.61 Hz, 2H) 2.84-3.03 (m, 2H) 4.22-4.44 (m, 3H) 5.26 (br s, 2H) 6.77 (s, 1H) 7.65 (s, 1H) 7.73-7.79 (m, 1H) 7.92 (s, 1H).

Workup

  1. customwas sparged with N2 for 15 min
  2. additiontreated with K2CO3 and Pd(PPh3)4
  3. customAfter sparging again with N2 for 5 min
  4. temperaturethe mixture was heated
  5. temperatureat reflux 4-6 h
  6. customThe 1,2-dimethoxyethane was removed in vacuo, water
  7. additionwas added
  8. extractionthe mixture extracted with DCM
  9. dry with materialThe combined DCM extracts were dried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f9515577d53042a9a43dcb7a94f6d834
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08378104B2

Reaction notes

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