1,4-Dioxane → HCID 59636648, compound

HRID 2098211Notes

Reaction equation

HRID 2098211 reaction equation
Br[C:2]1[N:3]=[CH:4][S:5][C:6]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].O1[CH2:20][CH2:19]OCC1>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>[N:3]1[CH:20]=[CH:19][N:7]=[CH:6][C:2]=1[C:2]1[N:3]=[CH:4][S:5][C:6]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 687870291239464-76-6

Product 1

HCID 59636648HCID 59636648, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of tert-butyl 4-bromothiazol-5-ylcarbamate (420 mg, 1.5 mmol), tetrakis(triphenylphosphine)palladium(0) (170 mg, 0.15 mmol) and 2-tributyl-stannylpyrazine (930 mg, 2.5 mmol) in anhydrous dioxane (4 mL) was heated to 140° C. in a microwave reactor for 2 h. The reaction mixture was then concentrated in vacuo and purified by flash chromatography (EtOAc/hexanes) to give the desired product (260 mg, 62%). 1H NMR (CDCl3) δ11.10 (s, 1H), 9.47 (d, J=1.4 Hz, 1H), 8.52 (t, J=2.0 Hz, 1H), 8.45 (d, J=2.7 Hz, 1H), 8.40 (s, 1H), 1.58 (s, 9H); MH+ 279.0.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-985e66031ff24cb6a676fa7dd827a48d
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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