Triphenylphosphine → tert-butyl 4-(2-(3-(3,5-difluorophenyl)-1-oxo-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperidine-1-carboxylate

HRID 331319Notes

Reaction equation

HRID 331319 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]=2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.BrC1C(=O)C2C(C=1C1C=CC=CC=1)=CC=C(O)C=2.O[CH2:45][CH2:46][CH:47]1[CH2:52][CH2:51][N:50]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:49][CH2:48]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:45][CH2:46][CH:47]4[CH2:48][CH2:49][N:50]([C:53]([O:55][C:56]([CH3:57])([CH3:59])[CH3:58])=[O:54])[CH2:51][CH2:52]4)=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]=2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 5363146Diisopropyl azodicarboxylateHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703174323-(3,5-difluorophenyl)-6-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 51001989tert-butyl 4-(2-(3-(3,5-difluorophenyl)-1-oxo-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperidine-1-carboxylateYield 66%

Procedure

The procedure of Step 6 of Example 1 was repeated except for using 3-(3,5-difluorophenyl)-6-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one obtained in Step 1 of Example 64 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, t-butyl 4-(2-hydroxyethyl)piperidin-1-carboxylate (2.0 eq) instead of 4-(2-hydroxyethyl)morpholine, using 2 equivalents of PPh3 and DIAD, and being stirred for 13 h to provide the title compound (80 mg, 66%).

Sources & evidence

ORD record
ord-4f08374c2e794b119286a9609281be8c
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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