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

HRID 531446노트

반응식

HRID 531446 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c6a1cba5708f4403b9ead3e340915243
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353107B2

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