Potassium Carbonate → HCID 46831220, compound

HRID 1848354Notes

Reaction equation

HRID 1848354 reaction equation
[CH:1]1([O:6][C:7](=[O:25])[NH:8][CH2:9][C:10]2([C:13]3[N:24]=[C:16]4[C:17]([O:22][CH3:23])=[CH:18][CH:19]=[C:20](I)[N:15]4[N:14]=3)[CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[C:32]([C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)#[N:33]>COCCOC.[Cl-].[Na+].O.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>[CH:1]1([O:6][C:7](=[O:25])[NH:8][CH2:9][C:10]2([C:13]3[N:24]=[C:16]4[C:17]([O:22][CH3:23])=[CH:18][CH:19]=[C:20]([C:38]5[CH:37]=[CH:36][CH:35]=[C:34]([C:32]#[N:33])[CH:39]=5)[N:15]4[N:14]=3)[CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 86661597HCID 86661597, compound

Product 1

HCID 46831220HCID 46831220, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In a screw cap vial [1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-carbamic acid cyclopentyl ester was dissolved in DME (0.45 mL) and 1 M K2CO3 (0.14 mL) under argon. 3-cyanophenyl boronic acid (0.021 g, 0.15 mmol) and Pd(PPh3)4 (4 mg, 0.004 mmol) were added. The suspension was shaken at 80° C. for 17 h after which brine was added, and the aqueous phase was extracted with DCM (×3). The combined organic phases were dried, filtered and concentrated. The crude product was purified by flash chromatography using EtOAc:toluene 1:1->2:1 as the eluent to afford the title compound as an oil.

Workup

  1. additionwas added
  2. extractionthe aqueous phase was extracted with DCM (×3)
  3. customThe combined organic phases were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d62b9f34fd2a4c9f840cebad93fac1ef
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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