Water → 4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-2,8-bis-trifluoromethyl-quinoline

HRID 2075819Notes

Reaction equation

HRID 2075819 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[C:5](=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([B:28]2[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]2)=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:33][C:31]1([CH3:34])[C:30]([CH3:35])([CH3:36])[O:29][B:28]([C:25]2[CH:24]=[CH:23][C:22]([CH2:21][O:13][C:11]3[C:10]4[C:5](=[C:6]([C:14]([F:15])([F:16])[F:17])[CH:7]=[CH:8][CH:9]=4)[N:4]=[C:3]([C:2]([F:18])([F:1])[F:19])[CH:12]=3)=[CH:27][CH:26]=2)[O:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178516135HCID 178516135, compound

Product 1

HCID 865986314-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-2,8-bis-trifluoromethyl-quinolineYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step 2A [Intermediate 4, G9591-157-1]: To a solution of 2,8-Bis-trifluoromethyl-quinolin-4-ol (3.85 g, 13.7 mmol, 1.1 equiv.) in DMF (40 mL) was added 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.7 g, 12.5 mmol, 1.0 equiv.) and K2CO3 (3.45 g, 24.92 mmol, 2.2 equiv.) under N2 atmosphere. The reaction mixture was stirred at room temperature overnight. The reaction was complete as determined by TLC. The reaction mixture was poured into cold water, the white precipitate formed was collected by filtration, washed with water, dried under vacuum to yield 4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-2,8-bis-trifluoromethyl-quinoline in 73% yield (4.95 g).

Workup

  1. customthe white precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3fc9ff84559249928c2782cf67368e1e
Source dataset
uspto-grants-2011_04
Patent number
US07923446B2

Reaction notes

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