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Potassium Phosphate, Tribasic → {1-[5-(1-methyl-1H-pyrazol-4-yl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester

HRID 2038772
Notes
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Reaction equation

HRID 2038772 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14]([C:23]3[CH:22]=[N:21][N:20]([CH3:19])[CH:24]=3)=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58431130[1-(5-Iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Product 1

HCID 67515892{1-[5-(1-methyl-1H-pyrazol-4-yl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl esterYield 125.9%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of [1-(5-iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (500 mg, 1.39 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 433 mg, 2.1 mmol) and Pd(dppf)Cl2.dichloromethane complex (113 mg, 0.14 mmol) in 1.5 mL of DME/H2O/EtOH (7:3:2) in a sealable microwave tube was added 1M aqueous K3PO4 solution (2.1 mL). The tube was sealed and heated in the microwave at 100° C. for 10 min. The crude reaction was filtered through a pad of silica gel, washing with MeOH, and concentrated. The residue was partitioned between 30 mL of EtOAc and 10 mL of water. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated to give an oil. This material was purified by normal phase flash chromatography on silica gel (0→3.5% MeOH/CH2Cl2) to give 0.55 g of {1-[5-(1-methyl-1H-pyrazol-4-yl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester as a brown solid. The compound was used in subsequent steps without further purification.

Workup

  1. customThe tube was sealed
  2. customThe crude reaction
  3. filtrationwas filtered through a pad of silica gel
  4. washwashing with MeOH
  5. concentrationconcentrated
  6. customThe residue was partitioned between 30 mL of EtOAc and 10 mL of water
  7. washThe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an oil
  12. customThis material was purified by normal phase flash chromatography on silica gel (0→3.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-31fcbbad7d6d49758e32409980170f31
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575360B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes