2-(Tributylstannyl)-1,3-thiazole → 4,4-Dimethyl-6-(3-thiazol-2-yl-phenyl)1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1725058Notes

Reaction equation

HRID 1725058 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:20]=[CH:19][C:11]3[NH:12][C:13](=[O:18])[O:14][C:15]([CH3:17])([CH3:16])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC>CN(C=O)C>[CH3:16][C:15]1([CH3:17])[O:14][C:13](=[O:18])[NH:12][C:11]2[CH:19]=[CH:20][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)[CH:3]=3)=[CH:9][C:10]1=2

Participants

4

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 98624116-(3-Bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 98589994,4-Dimethyl-6-(3-thiazol-2-yl-phenyl)1,4-dihydro-benzo[d][1,3]oxazin-2-oneYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-(3-bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (0.25 g, 0.75 mmol), tri-n-butyl-thiazol-2-yl tin (0.5 g, 1.3 mmol) in DMF (5 mL) was degassed to remove oxygen and then heated under nitrogen at 90° C. for 3 hours. The reaction mixture was cooled to rt and treated with ice-water (70 mL). Ethyl acetate (100 mL) was added and organic layer was separated, washed with brine, and dried (MgSO4). After removal of solvent, the residue was purified by a silica gel column (hexane:ethyl acetate/1:1) to give the title compound as a white solid (60 mg, 23%): mp 223-224° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 9.13 (s, 1H), 8.45 (s, 1H), 7.94 (bs, 1H), 7.67-7.61 (m, 4H), 7.53 (t, 1H, J=7.68 Hz), 7.00 (d, 1H, J=8.81 Hz), 1.7 (s, 6H); MS (APCI) m/z 337([M+H]+, 100%); Anal. Calc. For C19H16N2O2S.0.25 H2O: C, 66.94; H, 4.88; N, 8.22. Found: C, 66.57; H, 4.65; N, 7.92.

Workup

  1. customwas degassed
  2. customto remove oxygen
  3. temperatureThe reaction mixture was cooled to rt
  4. additiontreated with ice-water (70 mL)
  5. additionEthyl acetate (100 mL) was added
  6. customorganic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customAfter removal of solvent
  10. customthe residue was purified by a silica gel column (hexane:ethyl acetate/1:1)

Sources & evidence

ORD record
ord-44b0d4ed687c4b85abadb645582d3eb0
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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