1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 24961821, compound

HRID 1662853Notes

Reaction equation

HRID 1662853 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH2:26]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[C:39](Br)[CH:38]=1)(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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.[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:26]([NH:33][S:34]([C:37]1[CH:38]=[CH:39][C:40]([CH3:43])=[C:41]([NH:1][C:2]2[CH:7]=[N:6][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([S:15](=[O:17])(=[O:16])[NH:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:11][CH:10]=3)=[N:4][CH:3]=2)[CH:42]=1)(=[O:36])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7213295N-Benzyl-3-bromo-4-methylbenzene-1-sulfonamideHCID 23665647Potassium tert-butoxideHCID 58748706HCID 58748706, compound

Product 1

HCID 24961821HCID 24961821, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of intermediate 45 (Example 93) (0.10 g, 0.28 mmol), N-benzyl-3-bromo-4-methyl-benzenesulfonamide (0.10 g, 0.29 mmol), Pd(OAc)2 (5 mg, 0.022 mmol), Xantphos (26 mg, 0.045 mmol) and potassium tert-butoxide (70 mg, 0.63 mmol) in a mixture of dioxane/DNIF (2/1, 3 mL) was sealed in a microwave reaction tube and irradiated with microwave at 150° C. for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM) to afford the title compound (0.10 g, 58%) as a white solid.

Workup

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 150° C. for 20 min
  3. customthe cap was removed
  4. filtrationthe resulting mixture filtered
  5. washthe filtered solid washed with DCM
  6. concentrationThe filtrate was concentrated
  7. customthe residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM)

Sources & evidence

ORD record
ord-df72e65fef484d8db79887f1aec82288
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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