Potassium Carbonate → HCID 58387138, compound

HRID 1045106Notes

Reaction equation

HRID 1045106 reaction equation
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1.[N:24]1[NH:25][C:26]([C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)=[CH:27][CH:28]=1.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.C(#N)C.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>[Cl:1][C:2]1[C:3]([C:32]2[CH:31]=[CH:30][C:29]([C:26]3[NH:25][N:24]=[CH:28][CH:27]=3)=[CH:34][CH:33]=2)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 45791081[4-(1H-Pyrazol-5-yl)phenyl]boronic acidHCID 59267806HCID 59267806, compound2×

Product 1

HCID 58387138HCID 58387138, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A 5 mL Biotage™ microwave vial was charged with 6-chloro-5-iodo-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (Intermediate 5, 73.2 mg, 0.150 mmol), 4-(2H-pyrazol-3-yl)-phenylboronic acid (33.9 mg, 0.180 mmol) and Pd(PPh3)4 (8.7 mg, 5 mol %) followed by dioxane (1.5 mL) and 1M aqueous K2CO3 (180 uL). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 130° C. for 10 min. The suspension was then diluted with EtOAc (5 mL) and washed with 1M aqueous K2CO3 (twice, 1 mL) and water (twice, 1 mL). The organic layer was evaporated to dryness in vacuo to give yellow oil. The oil was dissolved in ACN and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The solvent was evaporated to dryness in vacuo to give the crude product as pale yellow solid. LR-MS (API-ES): calculated for C23H27ClN4O3SSi 502.1, observed m/e 503.0 (M+H)+ (Rt 3.30 min).

Workup

  1. washwashed with 1M aqueous K2CO3 (twice, 1 mL) and water (twice, 1 mL)
  2. customThe organic layer was evaporated to dryness in vacuo
  3. customto give yellow oil
  4. customThe solvent was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2983f486e5d545c7ad155a0d56a00ff1
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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