2-(Tributylstannyl)-1,3-thiazole → 5-(1,3-Thiazol-2-yl)pyridin-3-amine

HRID 2201094Notes

Reaction equation

HRID 2201094 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)CCC.I[C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[N:24][CH:25]=1>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:7]1[CH:8]=[CH:9][N:10]=[C:6]1[C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[N:24][CH:25]=1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 242291885-Iodo-pyridin-3-ylamine

Product 1

HCID 675097085-(1,3-Thiazol-2-yl)pyridin-3-amineYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

The mixture of 2-tributylstannylthiazole (2.24 g, 6.00 mmol), 5-iodopyridin-3-ylamine (1.10 g, 5.00 mmol) and Pd(Ph3P)4 (580 mg, 0.5 mmol) in 50 mL toluene was degassed using Ar. The mixture was then stirred under Ar at 115° C. for 3 h. The mixture was concentrated and subjected to flash column (0 to 7% MeOH in DCM) to isolate 5-(thiazol-2-yl)pyridin-3-amine (740 mg, 84% yield).

Workup

  1. customwas degassed
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-5ac406134c324beaab42f2121193a869
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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