1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761791, compound

HRID 528622Notes

Reaction equation

HRID 528622 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][O:11][CH3:12].[CH3:13][O:14][C:15]1[CH:40]=[CH:39][C:18]([CH2:19][N:20]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:21]([C:24]2[CH:25]=[CH:26][C:27]3[NH:32][CH2:31][CH2:30][O:29][C:28]=3[CH:33]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=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]>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:21]([C:24]2[CH:25]=[CH:26][C:27]3[N:32]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[O:8][CH2:9][CH2:10][O:11][CH3:12])[CH2:31][CH2:30][O:29][C:28]=3[CH:33]=2)(=[O:23])=[O:22])=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 137209681-Bromo-2-(2-methoxyethoxy)benzeneHCID 23676156Sodium t-butoxideHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Product 1

HCID 89761791HCID 89761791, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-bromo-2-(2-methoxyethoxyl)benzene (302.0 mg, 1.31 mmol), INTERMEDIate M (500 mg, 1.19 mmol), Pd2(dba)3 (76.0 mg, 0.0837 mmol), Xantphos (69.0 mg, 0.119 mmol) and sodium-tert-butoxide (229.0 mg, 2.39 mmol) in toluene (10 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was subjected for heating at 100° C. for 1 h under microwave. 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: 12% ethyl acetate in hexane) to get N-(4-methoxybenzyl)-4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 44.2%) as yellow solid. MS (ESI, positive ion) m/z: 568.03 (M+1).

Workup

  1. customwas degassed with nitrogen for 10 minutes
  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: 12% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-651770def0d14f7a9e004fab761c2430
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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