Dimethylformamide → HCID 86690779, compound

HRID 1471741Notes

Reaction equation

HRID 1471741 reaction equation
Br[C:2]1[C:7]([CH2:8][O:9][C:10]2[C:11]([CH:18]3[O:22][CH2:21][CH2:20][O:19]3)=[CH:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:23][N:24](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:11]1[CH:12]=[C:13]([O:16][CH3:17])[N:14]=[CH:15][C:10]=1[O:9][CH2:8][C:7]1[C:2]([C:23]#[N:24])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86690777HCID 86690777, compound

Product 1

HCID 86690779HCID 86690779, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
125 °C

Procedure

A mixture of 5-((2-bromopyridin-3-yl)methoxy)-4-(1,3-dioxolan-2-yl)-2-methoxypyridine (1.1 g, 3.0 mmol, 1 eq.), Zn (CN)2 (704 mg, 6.0 mmol, 2.0 eq.), and Pd(PPh3)4 (346 mg, 0.3 mmol, 0.2 eq.) in DMF (10 mL) was heated at 125° C. for 2 h under N2. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinonitrile (820 mg, 84%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.71 (d, J=4.6 Hz, 1H), 8.12 (dd, J=8.0, 0.7 Hz, 1H), 7.88 (s, 1H), 7.60 (dd, J=8.0, 4.7 Hz, 1H), 6.95 (s, 1H), 6.16 (s, 1H), 5.37 (s, 2H), 4.18-4.00 (m, 4H), 3.92 (s, 3H). LRMS (M+H+) m/z 314.1.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified on silica gel using
  5. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-050747fe4fed4023afc97ae1fcd26502
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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