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

HRID 915760
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HRID 915760 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-72f96e85368644489c26cec88a8d2252
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07268135B2

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