2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane → HCID 66910071, compound

HRID 1942119Notes

Reaction equation

[C:1]12([CH2:14][CH2:13][CH2:12][CH2:11]1)[C:9]1[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:3][C:2]2=[O:10].BrC1C=NC=CC=1/C(=[CH:30]\[N:31]([CH3:33])[CH3:32])/C(C1CCCC1)=O.CC([O-])(C)C.[Na+].C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C>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]>[CH3:30][N:31](/[CH:33]=[C:3]1\[C:2](=[O:10])[C:1]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4]\1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:32]

Participants

Conditions

Temperature: 110 °C

Procedure

(3′Z)-3′4(Dimethylamino)methylidene)spiro[cyclopentane-1,1′-inden]-2′(3′H)-one (123) To a degassed solution of 2-(3-bromopyridin-4-yl)-1-cyclopentyl-3-(dimethylamino)prop-2-en-1-one (122) (4.738 g, 14.63 mmol) and sodium 2-methylpropan-2-olate (4.23 g, 44 mmol) in 20 ml of anhydrous toluene was added Pd2(dba)3 (0.806 g, 0.879 mmol) and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phospha-bicyclo[3.3.3]undecane (0.603 g, 1.757 mmol) under an atmosphere of nitrogen. The reaction was heated to 110° C. for 1.5 hours before it was cooled to 20° C. and concentrated under vacuum to give mainly (3′Z)-3′-((dimethylamino)methylidene)spiro[cyclopentane-1,1′-inden]-2′(3′H)-one (123). LCMS-ESI (POS), M/Z, M+1: Found 243.1.

Workup

temperaturewas cooled to 20° C.
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-55ed8e4122db46eb82524fd18453b59d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389533B2

Reaction notes

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