HCID 86674839, compound → HCID 53236853, compound

HRID 1897593Notes

Reaction equation

HRID 1897593 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:18]=2[CH:19]=[O:20])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>C1COCC1>[Cl:4][C:5]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:18]=2[CH:19]([OH:20])[CH3:1])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 86674839HCID 86674839, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 53236853HCID 53236853, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methylmagnesium bromide (519 μl, 1.558 mmol) was added dropwise to a solution of 2-chloro-4-(4-formylpyridin-3-yl)benzonitrile (126 mg, 0.519 mmol) in dry THF (15 mL) at −50° C. The resulting mixture was slowly warmed up to 0° C. during 2 hr. The reaction was quenched by NH4Cl (solution). After extraction with CH2Cl2, dry over Na2SO4, filtration, concentration again, the residue was purified by column (CH2Cl2-MeOH, v/v, 1-3.5%) and yielded 120 mg of 2-chloro-4-(4-(1-hydroxyethyl)pyridin-3-yl)benzonitrile. ESI-MS m/z: 259 [M+1]+, Retention time 1.11 min; 1H-NMR (MeOD, 400 MHz) δ 1.29 (d, J=6.4 Hz, 3H), 4.83 (q, J=6.4 Hz, 1H), 7.50 (dd, J=8.0, 1.6 Hz, 1H), 7.71 (d, J=1.6 Hz, 1H), 7.73 (d, J=5.6 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 8.35 (s, 1H), 8.61 (d, J=5.6 Hz, 1H).

Workup

  1. customThe reaction was quenched by NH4Cl (solution)
  2. extractionAfter extraction with CH2Cl2
  3. dry with materialdry over Na2SO4, filtration, concentration again
  4. customthe residue was purified by column (CH2Cl2-MeOH, v/v, 1-3.5%)

Sources & evidence

ORD record
ord-48a1d0be36a14020b4da3e0c69a2fc37
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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