Triethylamine → Methyl-(5-trimethylsilanylethynyl-pyridin-2-yl)-amine

HRID 471398노트

반응식

HRID 471398 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][Si:11]([CH3:15])([CH3:14])[C:12]#[CH:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.C1CCCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][NH:8][C:5]1[CH:4]=[CH:3][C:2]([C:13]#[C:12][Si:11]([CH3:15])([CH3:14])[CH3:10])=[CH:7][N:6]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 156456635-Bromo-N-methylpyridin-2-amine

생성물 1

HCID 66705950Methyl-(5-trimethylsilanylethynyl-pyridin-2-yl)-amine

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8078Cyclohexane용매HCID 8857Ethyl Acetate용매

실험 절차

The title compound is synthesized according to general procedure GP2 starting from 4.3 g (23.0 mmol) 5-bromo-2-methylamino-pyridine and 4.5 mL (32.2 mmol) 1-trimethylsilyl-ethyne using 134 mg (0.71 mmol) CuI, 601 mg (2.3 mmol) triphenylphosphine, 420 mg (0.60 mmol) PdCl2(PPh3)2 and 32 mL (101 mmol) triethylamine in 40 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate and small amounts of cyclohexane, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient. Yield: 4.0 g (85%).

후처리

  1. extractionthe organic phase is extracted with water and brine
  2. customThe product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient

출처 및 근거

ORD 기록
ord-71264766d05b432a907f6194ca01b16a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633183B2

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