1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761875, compound

HRID 528627Notes

Reaction equation

HRID 528627 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1.[CH3:14][O:15][C:16]1[CH:41]=[CH:40][C:19]([CH2:20][N:21]([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)[S:22]([C:25]2[CH:26]=[CH:27][C:28]3[NH:33][CH2:32][CH2:31][O:30][C:29]=3[CH:34]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)[S:22]([C:25]2[CH:26]=[CH:27][C:28]3[N:33]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[C:8]4[CH:9]=[N:10][CH:11]=[N:12][CH:13]=4)[CH2:32][CH2:31][O:30][C:29]=3[CH:34]=2)(=[O:24])=[O:23])=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 83824282HCID 83824282, compoundHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Product 1

HCID 89761875HCID 89761875, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(2-bromophenyl)pyrimidine (251 mg, 1.07 mmol), INTERMEDIate M (300 mg, 7.17 mmol), Pd2(dba)3 (65 mg, 0.0717 mmol), Xantphos (82 mg, 0.143 mmol) and sodium-tert-butoxide (137 mg, 1.43 mmol) in toluene (8 mL) was degassed for 10 min. The reaction mixture was subjected to microwave heating for 1 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 the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 35% ethyl acetate in hexane) to get N-(4-methoxybenzyl)-4-(2-(pyrimidin-5-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as yellow solid (250 mg, 41.0%); MS (ESI, positive ion) m/z: 572.0 (M+1).

Workup

  1. customwas degassed for 10 min
  2. additionAfter completion, the reaction mixture was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude material which
  7. customwas purified by combiflash column chromatography (column size: 12 g; elution: 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a197fc0734e54873a564ebb56f9f8363
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

Loading…