Pyridine → HCID 3490450, compound

HRID 1721830Notes

Reaction equation

HRID 1721830 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][O:11]2)=[CH:6][C:5]=1[F:21])([OH:3])=[O:2].N1C=CC=CC=1.S(Cl)(Cl)=O.O[C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[C:35]([F:41])[CH:34]=1>C(OCC)C>[C:37]([C:36]1[CH:39]=[CH:40][C:33]([O:2][C:1]([C:4]2[CH:9]=[CH:8][C:7]([B:10]3[O:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][O:11]3)=[CH:6][C:5]=2[F:21])=[O:3])=[CH:34][C:35]=1[F:41])#[N:38]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 24386Thionyl ChlorideHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 4258246Benzoic acid, 2-fluoro-4-(5-pentyl-1,3,2-dioxaborinan-2-yl)-

Product 1

HCID 3490450HCID 3490450, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture comprising 0.004 mole of 2-(4-carboxy-3-flurophenyl)-5-pentyl-1,3,2-dioxaborinane, 0.32 ml of pyridine, 0.32 ml of thionyl chloride in 50 ml of anhydrous diethyl ether is stirred for 1 hour. Then 0.004 mole of 4-hydroxy-2-fluorobenzonitrile and 1 ml of pyridine are added. The mixture is allowed to stand overnight and then filtered. The residue obtained after distilling off the solvent is crystallized from a mixture of hexane and ethyl alcohol. The yield of the compound (VIs) is 60%. M.p. 63° C.

Workup

  1. waitto stand overnight
  2. filtrationfiltered
  3. customThe residue obtained
  4. distillationafter distilling off the solvent
  5. customis crystallized from a mixture of hexane and ethyl alcohol

Sources & evidence

ORD record
ord-1ba647842b9f40d9b1d34d5675c76972
Source dataset
uspto-grants-1989_08
Patent number
US04853150

Reaction notes

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