2-(Tributylstannyl)-1,3-thiazole → HCID 22405335, compound

HRID 440775Notes

Reaction equation

HRID 440775 reaction equation
I[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][N:33]=1)CCC>C1(C)C=CC=CC=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>[S:30]1[CH:31]=[CH:32][N:33]=[C:29]1[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 15298021HCID 15298021, compound

Product 1

HCID 22405335HCID 22405335, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1.1 g of 10,11-dihydro-10-(4-iodobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 1.49 g of 2-(tributylstannyl)thiazole (Reference Example 48) in 50 ml of toluene under nitrogen is added 0.2 g of tetrakis(triphenylphosphine)palladium and the mixture heated to 120° C. for 16 hours. The toluene is evaporated in vacuo to a residue which is columned on silica gel by elution with 7:1 to 1:1 ethyl acetate:hexane to give 0.62 g of the desired product as an amphorous solid; M+H=372.3; M+Na=395.3.

Workup

  1. customThe toluene is evaporated in vacuo to a residue which
  2. washis columned on silica gel by elution with 7:1 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-fda5d0bf02894a378544bb510aa42be0
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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