Dimethylformamide → HCID 57634137, compound

HRID 2109721Notes

Reaction equation

HRID 2109721 reaction equation
[Cl-].[Li+].Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[CH:7]2.C([Sn](CCCC)(CCCC)[C:19]1[S:23][C:22]([NH:24][C:25](=[O:27])[CH3:26])=[N:21][CH:20]=1)CCC.CN(C=O)C>CCOC(C)=O.O.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>[CH:10]1[C:11]2[C:6](=[CH:5][C:4]([C:19]3[S:23][C:22]([NH:24][C:25](=[O:27])[CH3:26])=[N:21][CH:20]=3)=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 3136816-BromoisoquinolineHCID 433294Lithium ChlorideHCID 16427128N-[5-(Tributylstannyl)-1,3-thiazol-2-yl]acetamide

Product 1

HCID 57634137HCID 57634137, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of lithium chloride (0.295 g, 6.94 mmol) (flame-dried), 6-bromoisoquinoline (0.1805 g, 0.868 mmol), and Pd(PPh3)4 (0.0501 g, 0.0434 mmol) in a microwave reaction vessel, was added a solution of N-(5-(tributylstannyl)thiazol-2-yl)acetamide (0.561 g, 1.30 mmol) in DMF (2.00 mL, 0.868 mmol). The mixture was sealed and heated at 100° C. (oil bath) overnight. After cooling, the mixture (solidified) was diluted with EtOAc and water (2 mL each) and sonicated for 10 minutes. The resulting mixture was filtered, and the solid was washed with water and more EtOAc to provide N-(5-(isoquinolin-6-yl)thiazol-2-yl)acetamide (0.2177 g, 0.808 mmol) as a yellow solid. LCMS (M+H+) 270.3 calc. for C14H12N3OS 270.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 12.32 (br s, 1H), 9.27 (s, 1H), 8.48 (d, J=5.67 Hz, 1H), 8.13-8.15 (m, 3H), 8.06 (d, J=7.20 Hz, 1H), 7.85 (d, J=5.67 Hz, 1H), 2.20 (s, 3H).

Workup

  1. customin a microwave reaction vessel
  2. customThe mixture was sealed
  3. temperatureAfter cooling
  4. customsonicated for 10 minutes
  5. filtrationThe resulting mixture was filtered
  6. washthe solid was washed with water and more EtOAc

Sources & evidence

ORD record
ord-849a77b7b3cb4e5b94af15924a432b91
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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