HCID 46222180, compound → HCID 86635881, compound

HRID 594177Notes

Reaction equation

HRID 594177 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[N:6]=1.C[Sn](C)(C)[C:20]1[CH:21]=[CH:22][C:23]([CH2:26][OH:27])=[N:24][CH:25]=1>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.C1(C)C=CC=CC=1>[OH:27][CH2:26][C:23]1[N:24]=[CH:25][C:20]([C:2]2[S:3][CH:4]=[C:5]([N:7]3[C:15](=[O:16])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8]3=[O:17])[N:6]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 46222180HCID 46222180, compoundHCID 68996675HCID 68996675, compound

Product 1

HCID 86635881HCID 86635881, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(2 bromothiazol-4-yl)-isoindole-1.3-dione (10.0 g, 32.3 mmol) and (5-trimethylstannyl-pyridin-2-yl)-methanol (12.2 g, 26.9 mmol) in abs. toluene (50 mL) was placed in sealed tube, degassed and filled with tetrakis(triphenylphosphine)palladium(0) (932 mg, 0.8 mmol). The reaction mixture was heated at 160° C. for 1.5 hr and filtered while the reaction mixture was hot. After being cooled to room temperature for 2 hr, a solid was filtered through fritted funnel, washed with toluene (30 mL) and dried on vacuum to provide the title compound (6.2 g, 75%) as a pale yellow solid. MS-ESI m/z 338.02 (M+H)+.

Workup

  1. customdegassed
  2. filtrationfiltered while the reaction mixture
  3. temperatureAfter being cooled to room temperature for 2 hr
  4. filtrationa solid was filtered through fritted funnel
  5. washwashed with toluene (30 mL)
  6. customdried on vacuum

Sources & evidence

ORD record
ord-ede302eeade64211b958f9bd5460126a
Source dataset
uspto-grants-2016_01
Patent number
US09242974B2

Reaction notes

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