1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761414, compound

HRID 528589Notes

Reaction equation

HRID 528589 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1I.[CH3:12][O:13][C:14]1[CH:39]=[CH:38][C:17]([CH2:18][N:19]([C:33]2[S:34][CH:35]=[CH:36][N:37]=2)[S:20]([C:23]2[CH:24]=[CH:25][C:26]3[NH:31][CH2:30][CH2:29][O:28][C:27]=3[CH:32]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=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]>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:31]1[CH2:30][CH2:29][O:28][C:27]2[CH:32]=[C:23]([S:20]([N:19]([CH2:18][C:17]3[CH:38]=[CH:39][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)[C:33]3[S:34][CH:35]=[CH:36][N:37]=3)(=[O:21])=[O:22])[CH:24]=[CH:25][C:26]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 448911892-Bromo-1-iodo-4-(1-methylethyl)benzeneHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide2×

Product 1

HCID 89761414HCID 89761414, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A microwave vial was charged with 2-bromo-1-iodo-4-isopropylbenzene (Oakwood, 0.117 g, 0.359 mmol), N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (INTERMEDIATE M, 0.150 g, 0.359 mmol), Xantphos (0.042 g, 0.072 mmol), Pd2(dba)3 (0.033 g, 0.036 mmol) and sodium tert-butoxide (0.069 g, 0.719 mmol). The mixture was diluted with toluene (3.59 ml), and purged with nitrogen, and stirred at 130° C. in the microwave for 30 minutes, until clean conversion to the desired product. After completion, the reaction was filtered over a plug of Celite, washing well with DCM. The filtrate was concentrated in vacuo. The crude material was purified using a 5-g SCX column (product eluted with methanol wash to yield 4-(2-bromo-4-isopropylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.175 g, 0.285 mmol, 79% yield) as an orange oil. m/z (ESI) 614.0 (M+H)+.

Workup

  1. custompurged with nitrogen
  2. filtrationAfter completion, the reaction was filtered over a plug of Celite
  3. washwashing well with DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude material was purified
  6. washeluted with methanol
  7. washwash

Sources & evidence

ORD record
ord-f1ba8034d6184b85b45ee083b9344418
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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