Potassium Carbonate → HCID 17965919, compound

HRID 1348915Notes

Reaction equation

HRID 1348915 reaction equation
[OH:1][C:2]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)([C:5]1[N:9]([CH3:10])[CH:8]=[N:7][CH:6]=1)[CH2:3][OH:4].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=1[Br:28].C(=O)([O-])[O-].[K+].[K+]>CN(C1C=CN=CC=1)C.CS(C)=O>[Br:28][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:20]=1[O:4][CH2:3][C:2]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)([OH:1])[C:5]1[N:9]([CH3:10])[CH:8]=[N:7][CH:6]=1)[C:24]#[N:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1235793-Bromo-4-fluorobenzonitrileHCID 17965983HCID 17965983, compound

Product 1

HCID 17965919HCID 17965919, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of Example 93C (1.19 g, 4.9 mmol), 4-fluoro-3-bromobenzonitrile (1.50 g, 7.5 mmol), DMAP (0.12 g, 1 mmol), and potassium carbonate (5.00 g, 36 mmol) in DMSO (13 mL) at room temperature was stirred for 16 hours, quenched with water (20 mL), treated with ethyl acetate (70 mL), and filtered. The filter cake was washed with water and dried at 40° C. under vacuum to provide 1.50 g (72% yield, HPLC purity 95.6%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.09 (d, 1H), 7.84-7.80 (m, 3H), 7.61-7.58 (m, 3H), 7.37 (d, 1H), 7.16 (d, 1H), 6.56 (br s, 1H), 4.67 (d, 1H), 4.52 (d, 1H), 3.19 (s, 3H).

Workup

  1. customquenched with water (20 mL)
  2. additiontreated with ethyl acetate (70 mL)
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-bf13e0e8dd414e1ab0e7271730585204
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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