4-Fluorobenzonitrile → HCID 178510095, compound

HRID 572232Notes

Reaction equation

HRID 572232 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)=[O:10])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[H-].[Na+].F[C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([O:18][C:26]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=3)[CH2:16][CH2:17]2)=[O:10])=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

5

Reactant 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 178522079HCID 178522079, compound

Product 1

HCID 178510095HCID 178510095, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 07086 (1.35 g, 4 mmol) in DMF (40 mL) was added 60% sodium hydride in oil (0.24 g, 6 mmol) portionwise at 0° C. After 10 min, 4-fluorobenzonitrile (0.73 g, 6 mmol) was added. The reaction mixture was allowed to slowly warm to room temperature overnight. The reaction was quenched by adding water and the resulting white precipitates were collected and washed with water. The collected solid was recrystallized from methanol to give the title compound, 1.5 g (86%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.83-8.78 (s, 1H), 8.08 (d, J=2 Hz, 1H), 7.75 (d, J=9 Hz, 2H), 7.57-7.47 (m, 2H), 7.13 (d, J=9 Hz, 2H), 6.37 (d, J=7 Hz, 1H), 4.55-4.41 (m, 1H), 3.62-3.43 (m, 1H), 2.15-1.83 (m, 4H), 1.60-1.30 (m, 4H).

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. customthe resulting white precipitates
  4. customwere collected
  5. washwashed with water
  6. customThe collected solid was recrystallized from methanol

Sources & evidence

ORD record
ord-d6113d848ea84099b550af7758d1bcb0
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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