1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761565, compound

HRID 528655Notes

Reaction equation

HRID 528655 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[C:30]1[CH:41]=[CH:40][CH:39]=[CH:38][C:31]=1[O:32][CH2:33][C:34]([CH3:37])([OH:36])[CH3:35].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.O>[OH:36][C:34]([CH3:37])([CH3:35])[CH2:33][O:32][C:31]1[CH:38]=[CH:39][CH:40]=[CH:41][C:30]=1[N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:21]=[C:12]([S:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]1=2

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 60880657HCID 60880657, compoundHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide2×

Product 1

HCID 89761565HCID 89761565, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M; 700 mg, 1.674 mmol), 1-(2-bromophenoxy)-2-methylpropan-2-ol (2.8 g, 11.722 mmol), Pd2(dba3)2 (96 mg, 0.1674 mmol), Xantphos (306 mg, 0.3349 mmol) and sodium-tert-butoxide (402 mg, 4.186 mmol) in toluene (15 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was subjected to microwave for 1 h at 100° C. After completion, 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 combiflash silica gel column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane) to yield 4-(2-(2-hydroxy-2-methylpropoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 88.2%). m/z (ESI) 582.1 (M+H)+.

Workup

  1. customwas degassed with nitrogen for 10 minutes
  2. customAfter completion, reaction mixture
  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 crude material, which
  7. customwas purified by combiflash silica gel column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ec693c748086475b94f4ec70b2ca0a07
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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