4-Iodobenzenesulfonyl chloride → HCID 22674075, compound

HRID 1005700Notes

Reaction equation

HRID 1005700 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][CH3:13])=[N:7][CH:6]=[CH:5]2.I[C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C([Sn](CCCC)(CCCC)[C:30]1[S:31][CH:32]=[CH:33][N:34]=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>[CH3:13][O:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][S:21]([C:18]3[CH:19]=[CH:20][C:15]([C:30]4[S:31][CH:32]=[CH:33][N:34]=4)=[CH:16][CH:17]=3)(=[O:23])=[O:22])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 73994-Iodobenzenesulfonyl chlorideHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 226740451-Methoxyisoquinolin-6-amine

Product 1

HCID 22674075HCID 22674075, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The compound (40 mg) obtained by the procedure of Example 1, except using 6-amino-1-methoxyisoquinoline (Preparation Example 43) and 4-iodobenzenesulfonyl chloride, 2-tri-n-butylstannylthiazole (136 mg), tetrakis(triphenylphosphine)palladium(0) (11 mg) were heated under reflux in toluene in nitrogen atmosphere for 1 hour. The solvent was evaporated and the residue was purified by silica gel column. The resulting crystals were recrystallized from methanol, to give the title compound (20 mg).

Workup

  1. temperaturewere heated
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel column
  4. customThe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-f849178b83384aca942cd675fd30b8e0
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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