1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 86731091, compound

HRID 1844424Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH:5]=[CH:6][CH:7]=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.[N:60]1([C:66]([O:68][CH2:69][C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)=[O:67])[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CCCCCC.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].CCOC(C)=O>[C:13]([O:12][C:11]([NH:10][C@@H:8]([C:4]1[CH:3]=[C:2]([N:63]2[CH2:62][CH2:61][N:60]([C:66]([O:68][CH2:69][C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)=[O:67])[CH2:65][CH2:64]2)[CH:7]=[CH:6][CH:5]=1)[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of Intermediate 33A (50 mg, 0.167 mmol) and Pd2(dba)3 (15.25 mg, 0.017 mmol) in toluene (2 mL) was added xantphos (28.9 mg, 0.050 mmol), benzyl piperazine-1-carboxylate (36.7 mg, 0.167 mmol), followed by sodium tert-butoxide (48.0 mg, 0.500 mmol). The reaction mixture was stirred at 70° C. for 16 h, and then filtered. The filtrate was concentrated and purified on ISCO using a 15 min gradient from 0 to 100% EtOAc in hexane to give Intermediate 33B (70 mg, 0.159 mmol, 96% yield). LC-MS (ESI) m/z 440.1 (M+H), RT=2.27 min (Method B).

Workup

filtrationfiltered
concentrationThe filtrate was concentrated
custompurified on ISCO
waitusing a 15 min

Sources & evidence

ORD record: ord-94c8a8d39022482dbd9905e724f7c88e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946430B2

Reaction notes

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