4-Iodobenzenesulfonyl chloride → HCID 22674075, compound

HRID 1173143Notes

Reaction equation

HRID 1173143 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 using 6-amino-1-methoxyisoquinoline (Production Example 43b) and 4-iodobenzenesulfonyl chloride in the same method as in Synthetic Example 1b, 2-tri-n-butylstannylthiazole (136 mg) and tetrakis(triphenylphosphine)palladium (0) (11 mg) were heated under reflux for one hour in toluene in a nitrogen atmosphere. After evaporating the solvent, 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. customAfter evaporating the solvent
  3. customthe residue was purified by silica gel column
  4. customThe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-7760b20f743043ccb1e5c3dc8c6ec991
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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