Triethylamine → 5-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 531446ノート

反応式

HRID 531446 の反応式
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.C(N(CC)CC)C.[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21]>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.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:21]#[C:20][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 900227685-Bromo-6-cyclopropyl-3-iodopyridin-2-amine

生成物 1

HCID 900223295-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Cuprous iodide (11.23 mg, 0.059 mmol) was added to a mixture of 5-bromo-6-cyclopropyl-3-iodopyridin-2-amine (1 g, 2.95 mmol), triethylamine (13.4 g, 132.75 mmol) and THF (4 mL) and the resultant mixture was purged with nitrogen gas. Ethynyltrimethylsilane (347.7 mg, 3.54 mmol) and Pd(PPh3)2Cl2 (41.36 mg, 0.059 mmol) were added and purged with argon. The resultant mixture was stirred under argon atmosphere for 5 hours. The mixture was concentrated to residue. Residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate and concentrated to get solid which was further purified on column (SiO2) using 15% ethyl acetate in hexane as eluent. This afforded 1.2 g (crude) of the pure compound.

後処理

  1. customthe resultant mixture was purged with nitrogen gas
  2. custompurged with argon
  3. concentrationThe mixture was concentrated to residue
  4. dissolutionResidue was dissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto get solid which
  9. customwas further purified on column (SiO2)

出典と根拠

ORDレコード
ord-c6a1cba5708f4403b9ead3e340915243
出典データセット
uspto-grants-2016_05
特許番号
US09353107B2

反応ノート

読み込み中…