Dimethylformamide → N-((R)-5-vinylindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

HRID 1039639Notes

Reaction equation

HRID 1039639 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:16][N:15]=1)=[O:13])[CH2:5]2.[CH2:27](C([Sn])=C(CCCC)CCCC)[CH2:28]CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH:27]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:16][N:15]=1)=[O:13])[CH2:5]2)=[CH2:28]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 53438229Tri(butyl)vinyltinHCID 66679917N-((R)-5-bromoindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

Product 1

HCID 66679809N-((R)-5-vinylindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of N-((R)-5-bromoindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide (1.70 g), tributylvinyltin (1.55 g), triphenylphosphine (85.5 mg), palladium(II) acetate (18.3 mg) and DMF (20 ml) was admixed under argon with triethylamine (7.4 ml) and heated to reflux for 4 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was filtered through silica gel. This afforded the product with the molecular weight of 364.45 (C22H24N2O3); MS (ESI): 365 (M+H+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. filtrationThe residue was filtered through silica gel
  8. customThis afforded the product with the molecular weight of 364.45 (C22H24N2O3)

Sources & evidence

ORD record
ord-df2f8d352a6842be90a5eb5223aac24a
Source dataset
uspto-grants-2013_10
Patent number
US08552199B2

Reaction notes

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