Potassium Carbonate → HCID 67338572, compound

HRID 1045108Notes

Reaction equation

HRID 1045108 reaction equation
Cl[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.[C:24]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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>[C:24]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:28][C:27]([C:3]2[CH:2]=[CH:22][C:6]3[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])=[N:9][C:5]=3[CH:4]=2)=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 59267806HCID 59267806, compound2×

Product 1

HCID 67338572HCID 67338572, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A 2 mL Biotage™ microwave vial was charged with 6-chloro-5-iodo-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (Intermediate 5, 49.0 mg, 0.100 mmol), biphenyl-4-boronic acid (24.0 mg, 0.120 mmol) and Pd(PPh3)4 (5.8 mg, 5 mol %) following by dioxane (1.0 mL) and 1M aqueous K2CO3 (120 uL). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 150° C. for 10 min. The microwave procedure was repeated two more times, before each irradiation additional Pd(PPh3)4 (2.9 mg, 2.5 mol %) was added. The reaction mixture was then diluted with EtOAc (5 mL), filtered and the resulting solution was evaporated to dryness in vacuo to give brown 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 crude product as colorless oil which was used in the next step without further purification. LR-MS (API-ES): calculated C26H29ClN2O3SSi 512.1, observed m/e 513.0 (M+H)+, 485.0, 455.0 (Rt 3.91 min).

Workup

  1. filtrationfiltered
  2. customthe resulting solution was evaporated to dryness in vacuo
  3. customto give brown oil
  4. customThe solvent was evaporated to dryness in vacuo
  5. customto give crude product as colorless oil which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-7d150d36af5549bdb89536d5de987b22
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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