Dimethylformamide → HCID 11690594, compound

HRID 1715685Notes

Reaction equation

HRID 1715685 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[S:28][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([S:42]([NH2:45])(=[O:44])=[O:43])=[CH:38][CH:37]=3)[N:30]=2)=[CH:26][CH:25]=1.CN(C)C=O.[C:51]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=1)#[CH:52]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[N:54]1[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=1[C:51]#[C:52][C:24]1[S:28][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([S:42]([NH2:45])(=[O:44])=[O:43])=[CH:38][CH:37]=3)[N:30]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80271Tri-o-tolylphosphineHCID 137268EthynylpyridineHCID 57446774HCID 57446774, compound

Product 1

HCID 11690594HCID 11690594, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
180 °C

Procedure

A 10 mL glass microwave reaction vessel with stir bar contained palladium acetate (5 mg, 22 μmol), tri-o-tolylphosphine (13 mg, 44 μmol), and 4-[4-(5-bromo-thiophen-2-yl)-pyrimidin-2-ylamino]-benzenesulfonamide (80 mg, 200 μmol). Anhydrous dimethylformamide (DMF) (3.5 mL), 2-ethynylpyridine (46 mg, 450 μmol), and triethylamine (50 μL) is added to the reaction vessel. The reaction vessel is sealed and heated to 180° C. for 660 seconds in a microwave reactor (Emrys Microwave Reactor, personal Chemistry AB, Uppsala, Sweden). The reaction is filtered through celite, concentrated, redissolved in dimethylsulfoxide (DMSO), and purified by reverse phase (RP) HPLC to obtain 10 mg of the title compound. LC/MS data (Condition A; molecular ion and retention time): m/z 434 (M+H); 2.52 min.

Workup

  1. customThe reaction vessel is sealed
  2. filtrationThe reaction is filtered through celite
  3. concentrationconcentrated
  4. dissolutionredissolved in dimethylsulfoxide (DMSO)
  5. custompurified by reverse phase (RP) HPLC

Sources & evidence

ORD record
ord-5c5e0463c576436aa1ab6c995fea9ff7
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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