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Triphenylphosphine → N-methyl-N-((S)-6-vinyl-1,2,3,4-tetrahydronaphthalen-2-yl)-5-cyclopropylmethoxypyridine-2-carboxamide

HRID 77426
Notes
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Reaction equation

HRID 77426 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([N:12]([CH3:26])[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)=[CH:17][N:16]=1)=[O:14])[CH2:6][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.C(N(C(C)C)CC)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:26][N:12]([C@H:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:27]=[CH2:28])[CH:3]=2)[CH2:8]1)[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)=[CH:17][N:16]=1)=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 53438229Tri(butyl)vinyltinHCID 66663511N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methyl-5-cyclopropylmethoxy-pyridine-2-carboxamide

Product 1

HCID 66663592N-methyl-N-((S)-6-vinyl-1,2,3,4-tetrahydronaphthalen-2-yl)-5-cyclopropylmethoxypyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N—((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methyl-5-cyclopropylmethoxypyridine-2-carboxamide (1.50 g), tributylvinyltin (1.37 g), palladium(II) acetate (16 mg), triphenylphosphine (76 mg), diisopropylethylamine (8.5 ml) and DMF (20 ml) was heated to 100° C. for 12 hours. The cooled reaction mixture was partitioned between ethyl acetate and sodium carbonate solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel. The product was thus obtained with the molecular weight of 362.48 (C23H26N2O2); MS (ESI): 363 (M+H+).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and sodium carbonate solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customThe product was thus obtained with the molecular weight of 362.48 (C23H26N2O2)

Sources & evidence

ORD record
ord-1447899c35d14568b6be2f084ccabe3f
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841290B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes