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

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]

Participants

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

customThe cooled reaction mixture
customwas partitioned between ethyl acetate and sodium carbonate solution
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel
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

Linked notes

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