1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66799276, compound

HRID 1193369Notes

Reaction equation

[CH2:1]([N:8]([CH3:15])[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=1.C(O[Na])(C)(C)C.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>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]>[CH2:1]([N:8]([CH3:15])[CH:9]1[CH2:14][CH2:13][N:12]([C:17]2[CH:22]=[N:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N-Benzyl-N-methylpiperidin-4-amine (3.947 mmol, 1.0 eq.), 5-bromo-2-methoxypyridine (614 μl, 4.737 mmol, 1.2 eq.) and t-BuONa (757 mg, 7.894 mmol, 2.0 eq.) were dissolved in toluene (12 ml) and degassed with argon. Xantphos (136 mg. 0.237 mmol, 0.06 eq.) and Pd2(dba)3 (72 mg, 0.079 mmol, 0.02 eq.) were then added and the mixture was heated for 4 hours at 90° C. After monitoring by TLC, the reaction mixture was concentrated under reduced pressure and purified by column chromatography (silica gel, 3% MeOH in DCM). Yield: 36% (450 mg, 1.447 mmol)

Workup

customdegassed with argon
concentrationthe reaction mixture was concentrated under reduced pressure
custompurified by column chromatography (silica gel, 3% MeOH in DCM)

Sources & evidence

ORD record: ord-d0c1c0085d7e44309a0b3be82f39c9a8
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680159B2

Reaction notes

Loading…