Tetrahydrofurfuryl alcohol → HCID 70309509, compound

HRID 331326Notes

Reaction equation

HRID 331326 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.BrC1[C:28](=[O:43])[C:29]2C(C=1C1C=CC=CC=1)=C[CH:32]=[C:31](O)[CH:30]=2.O1CCCC1CO.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][CH2:32][CH:31]4[CH2:30][CH2:29][CH2:28][O:43]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 7360Tetrahydrofurfuryl alcoholHCID 11776TriphenylphosphineHCID 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 70309509HCID 70309509, compoundYield 7%

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, (tetrahydrofuran-2-yl)methanol (2.0 eq) instead of 4-(2-hydroxyethyl)morpholine, using 2 equivalents of PPh3 and DIAD, being stirred for 17 h, and being purified by prep. HPLC (20% H2O/CH3CN and 30% H2O/CH3CN) to provide the title compound (7%).

Workup

  1. custombeing purified by prep

Sources & evidence

ORD record
ord-d6c072a6305346ebb9090ba07e0feebd
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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