Potassium Carbonate → HCID 46831221, compound

HRID 1848357Notes

Reaction equation

HRID 1848357 reaction equation
I[C:2]1[N:7]2[N:8]=[C:9]([C:11]3([CH2:14][NH:15][C:16]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[O:17])[CH2:13][CH2:12]3)[N:10]=[C:6]2[C:5]([O:23][CH3:24])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)#[N:32]>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>[C:31]([C:33]1[CH:38]=[C:37]([C:2]2[N:7]3[N:8]=[C:9]([C:11]4([CH2:14][NH:15][C:16]([N:18]5[CH2:22][CH2:21][CH2:20][CH2:19]5)=[O:17])[CH2:12][CH2:13]4)[N:10]=[C:6]3[C:5]([O:23][CH3:24])=[CH:4][CH:3]=2)[CH:36]=[CH:35][CH:34]=1)#[N:32]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 86661598HCID 86661598, compound

Product 1

HCID 46831221HCID 46831221, compound

Reagents, catalysts & solvents 3

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

Procedure

In a screw cap vial pyrrolidine-1-carboxylic acid [1-(5-iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-amide 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 DCM:MeOH 97:3 as the eluent to afford the amorphous title compound.

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-67e77865b59a4b6889e097f0b3559463
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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