Sodium Cyanide → HCID 67346964, compound

HRID 1676403Notes

Reaction equation

HRID 1676403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17](I)[S:18][C:11]=12)[NH2:5].[C:20]([Cu])#[N:21].[C-]#N.[Na+]>CN(C=O)C>[NH2:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[CH:16]=[C:17]([C:20]#[N:21])[S:18][C:11]=23)=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)anilineHCID 178418546HCID 178418546, compound

Product 1

HCID 67346964HCID 67346964, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)aniline (Example 6, Step A; 0.50 g, 1.3 mmol) and CuCN (0.14 g, 1.6 mmol) was refluxed for 90 minutes in DMF (5 mL). The residue was poured into 25% aq. NaCN (30 mL), extracted with CHCl3, dried over MgSO4, and concentrated. The crude was purified by silica gel flash column chromatography (0.5% MeOH in CH2Cl2) to afford 0.179 g (49%) of the desired product. LRMS (APCI pos) m/e 286.2 (M+1). 1H-NMR (400 MHz, CDCl3) δ 8.62 (d, 1H), 8.08 (s, 1H), 7.05 (t, 1H), 6.67 (d, 1H), 6.53 (m, 2H), 3.87 (s, 2H); 19F-NMR (376 MHz, CDCl3) δ −128.4.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude was purified by silica gel flash column chromatography (0.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-dfa407ff557d4bb58dc370c34c0b73e5
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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