Nitrogen → HCID 19738077, compound

HRID 2255532Notes

Reaction equation

HRID 2255532 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([Sn](C)(C)C)=[CH:3][CH:2]=1.N#N.Br[C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[C:17]#[N:18]>C1(C)C=CC=CC=1.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>[C:17]([C:16]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:15]=1[C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)#[N:18]

Participants

6

Reactant 3

HCID 947NitrogenHCID 936542-Bromo-5-fluorobenzonitrileHCID 617834Stannane, trimethyl(4-methylphenyl)-

Product 1

HCID 19738077HCID 19738077, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of p-tolyltrimethyltin (1.26 g; 4.96 mmol) in dry toluene (8 mL) was degassed with a stream of N2 for ca. 5 min. To this solution under N2 was added 2-bromo-5-fluoro-benzonitrile (0.901 g; 4.51 mmol) and Pd(PPh3)4 (260 mg; 5 mol %). The reaction was stirred at reflux under N2 for 12 hr and then cooled to room temperature. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The product was purified by flash chromatography on a silica column eluting with Hex/CH2Cl2 to afford 0.606 g (64%) of the title compound as a slightly yellow solid. 1H-NMR (300 MHz, CDCl3) δ 2.40 (s, 3H), 7.28 (d, 2H), 7.34 (dd, 1H), 7.40 (d, 2H), 7.44 (t, 1H), 7.46 (dd, 1H); FAB mass spectrum, m/e 211 (m+, calcd for C14H10NF, 211).

Workup

  1. temperatureat reflux under N2 for 12 hr
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe product was purified by flash chromatography on a silica column
  5. washeluting with Hex/CH2Cl2

Sources & evidence

ORD record
ord-ba2e687dc6344dc6a96f10f75489edb0
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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