Triethylamine → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carbonitrile

HRID 888912노트

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HRID 888912 반응식
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.Br[C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:20]#[N:21])[NH:15]2.C(N(CC)CC)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[C:14]([C:20]#[N:21])[NH:15]3)[O:3]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 591513014-Bromo-1H-indole-2-carbonitrile

생성물 1

HCID 591513254-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carbonitrile수율 66%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

4,4,5,5-Tetramethyl-[1,3,2]dioxaborolane (2.1 mL, 14.5 mmol) was added drop-wise to a mixture of 4-bromo-1H-indole-2-carbonitrile (1.27 g, 5.8 mmol), palladium acetate (33 mg, 0.145 mmol), triethylamine (1.21 mL, 8.7 mmol) and 2-(dicyclohexylphosphino)biphenyl (203 mg, 0.58 mmol) in dioxane at 80° C. The reaction mixture was stirred at 80° C. for 5 h then allowed to stand at RT overnight. The reaction mixture was diluted with DCM and washed with water, then the organic layer was isolated, dried (MgSO4) then concentrated in vacuo. The resultant crude material was purified by column chromatography to afford the title compound as a brown solid (1.02 g, 66%).

후처리

  1. waitto stand at RT overnight
  2. washwashed with water
  3. customthe organic layer was isolated
  4. dry with materialdried (MgSO4)
  5. concentrationthen concentrated in vacuo
  6. customThe resultant crude material was purified by column chromatography

출처 및 근거

ORD 기록
ord-6550cbdd2666412183585a2d7dc4063b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252792B2

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