Tributylvinyltin → N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528651Notes

Reaction equation

HRID 528651 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[C:15]([S:18]([N:21]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:20])=[O:19])[CH:16]=[CH:17][C:9]1=2.[CH2:36]([Sn](CCCC)(CCCC)C=C)[CH2:37]CC>CN(C=O)C.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>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:21]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:18]([C:15]2[CH:16]=[CH:17][C:9]3[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH:36]=[CH2:37])[CH2:13][CH2:12][O:11][C:10]=3[CH:14]=2)(=[O:20])=[O:19])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 897618114-(2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Product 1

HCID 89761662N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamideYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1.2 g, 2.626 mmol), tributyl(vinyl)stannane (3.0 g, 10.5 mmol, Finar), Pd(PPh3)4 (303 mg, 0.131 mmol) in DMF (15 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was subjected to microwave irradiation for 2 h at 100° C. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain crude material which was purified by combi flash column chromatography (column size: 12 g; elution: 0-5% ethyl acetate in hexane) to get N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (750 mg, 68.0%) as a yellow solid. m/z (ESI) 520.1 (M+H)+.

Workup

  1. customwas degassed with nitrogen for 10 minutes
  2. customirradiation for 2 h at 100° C
  3. additionAfter completion, the reaction mixture was diluted with water (10 mL)
  4. extractionextracted with ethyl acetate (3×15 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain crude material which
  8. customwas purified by combi flash column chromatography (column size: 12 g; elution: 0-5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-067fbf77a95f4abb8d2edab5b8d6fa37
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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