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

HRID 471398ノート

反応式

HRID 471398 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-71264766d05b432a907f6194ca01b16a
出典データセット
uspto-grants-2014_01
特許番号
US08633183B2

反応ノート

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