Potassium Carbonate → HCID 58367196, compound

HRID 1891501Notes

Reaction equation

HRID 1891501 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[CH:6]=1.[C:8]([C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18])#[N:9].C(=O)([O-])[O-].[K+].[K+]>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.COCCOC.O>[Br:7][C:5]1[CH:6]=[C:2]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH:17]([CH3:19])[CH3:18])=[C:10]([CH:11]=2)[C:8]#[N:9])[S:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2724560Thiophene, 2,4-dibromo-HCID 49757979{3-Cyano-4-[(propan-2-yl)oxy]phenyl}boronic acid

Product 1

HCID 58367196HCID 58367196, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A 2 mL microwave vial was charged with 2,4-dibromothiophene (20 mg, 0.08 mmol), (3-cyano-4-isopropoxyphenyl)boronic acid (17 mg, 0.08 mmol), potassium carbonate (35 mg, 0.25 mmol) and 3:1 mixture of DME/H2O (4 mL). The reaction mixture was degassed by bubbling N2 through the stirred solution for 10 min. Pd(PPh3)4 (7 mg, 0.006 mmol) was added and the solution degassed for an additional 2 min. The vial was subjected to microwave irradiation at 70° C. for 30 min or until starting material consumed. 5-(4-bromothiophen-2-yl)-2-isopropoxybenzonitrile THIO INT-3 was used in the next experiment without purification. LCMS-ESI (m/z) calculated for C14H12BrNOS: 320.9; no M+ observed, tR=4.15 min.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling N2 through the stirred solution for 10 min
  3. customthe solution degassed for an additional 2 min
  4. customirradiation at 70° C. for 30 min
  5. customconsumed
  6. custom5-(4-bromothiophen-2-yl)-2-isopropoxybenzonitrile THIO INT-3 was used in the next experiment without purification

Sources & evidence

ORD record
ord-48b81f05342c4525b96fadac59152aef
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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