6-Chloro-3-pyridinecarbonitrile → HCID 68382772, compound

HRID 603454Notes

Reaction equation

HRID 603454 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.FC(F)(F)C(O)=O.[NH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C@H:27]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][CH2:25]2>CC#N.O1CCOCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[C@H:27]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][CH2:25]3)=[N:3][CH:4]=1)#[N:7]

Participants

5

Reactant 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 86604596HCID 86604596, compound

Product 1

HCID 68382772HCID 68382772, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloronicotinonitrile (0.78 g, 5.54 mmol) and ethyl [(1S)-5-(3-aminopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate trifluoroacetate (Example 263, 2.17 g, 5.54 mmol) in CH3CN (14 mL) and 1,4-dioxane (14 mL) was heated to reflux for 8 h, cooled to rt, and then concentrated under reduced pressure. The product (1.14 g, 54%) was isolated after column chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 8.20 (s, 1H), 7.45 (dd, 1H), 6.94 (d, 1H), 6.67 (s, 1H), 6.58 (dd, 1H), 6.32 (d, 1H), 5.42 (b, 1H), 4.02 (q, 2H), 3.95 (t, 2H), 3.50-3.35 (m, 3H), 2.85-2.68 (m, 2H), 2.59 (dd, 1H), 2.32-2.20 (m, 2H), 2.00 (qt, 2H), 1.70-1.60 (m, 1H), 1.17 (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ab74d4e9f044768a0efb9e3578c747f
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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