1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 86721866, compound

HRID 1049006Notes

Reaction equation

HRID 1049006 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]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]>[C:34]([O:33][C:31]([N:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[N:11]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=2)[CH2:26][CH2:27]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 12682914-Amino-1-Boc-piperidineHCID 23676156Sodium t-butoxideHCID 86721865HCID 86721865, compound

Product 1

HCID 86721866HCID 86721866, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-bromo-N-(4-fluoro-benzyl)-N-isobutyl-benzenesulfonamide (200 mg, 500 μmol), 4-amino-1-boc-piperidine (120 mg, 600 μmol), Pd2(dba)3 (46 mg, 50 μmol), XantPhos (29 mg, 50 μmol), and sodium tert-butoxide (106 mg, 1.1 mmol) in toluene (5 mL) was degassed with nitrogen then heated at 125° C. for 30 minutes in a microwave reactor. Water was added then extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated and purified by silica gel column chromatography (0-50% EtOAc in cyclohexane) to give 4-{4-[(4-fluoro-benzyl)-isobutyl-sulfamoyl]-phenylamino}-piperidine-1-carboxylic acid tert-butyl ester (208 mg, 80%). LCMS (m/z, Method A) ES− 518[M−1]−.

Workup

  1. customwas degassed with nitrogen
  2. additionWater was added
  3. extractionthen extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (0-50% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-5e8444072f884bc8b61f52e6faa0baf5
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

Loading…