Trimethylsilylacetylene → HCID 86739598, 화합물

HRID 358239

반응식

HRID 358239 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]3[C:17]4[N:16]=[CH:15][N:14]=[CH:13][C:12]=4[CH:11]=[CH:10][C:9]=3[C:4]=2[N:3]=[CH:2]1.[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])#[CH:19]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH3:21][Si:20]([C:18]#[C:19][C:4]1[CH:5]=[C:6]([C:13]2[C:12]3[CH:11]=[CH:10][C:9]4[C:4]5[N:3]=[CH:2][NH:1][C:5]=5[CH:6]=[CH:7][C:8]=4[C:17]=3[N:16]=[CH:15][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:23])[CH3:22]

참가 물질

4

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 67938489HCID 67938489, 화합물

생성물 1

HCID 86739598HCID 86739598, 화합물수율 70.5%

시약·촉매·용매 1

HCID 22504574Toluene triethylamine용매

실험 절차

A slurry of 3.00 g (9.02 mmoles) of 6-bromophenyl)benzimidazoquinazoline, 100 mg of diacetatobis(triphenylphosphine)palladium[II] in 150 ml of 2:1 triethylamine-toluene was heated to 100° C. under argon and then treated with dropwise addition of 1.57 g (16.0 mmoles) of ethynyltrimethylsilane. After 3.5 hours, the mixture was cooled and filtered. The filtrate was diluted with 100 ml of ether, washed with 200 ml each of 5% hydrochloric acid and water, and then dried over magnesium sulfate. Concentrating the clear solution yielded a solid mass which upon trituration with hexane gave 2.21 g (56.5 mmoles, 70.5%) of 6-(m-trimethylsilylethynylphenyl)benzimidazoquinazoline: ir (KBr): 3077 (medium, sharp, C-H), 2960 (medium, sharp, SiCH), 2155 (strong, sharp, C≡C), 1621, 1587 (v. strong, sharp, C=N), 1524, 1456, 1441, 1355, 1325 (strong, sharp, C=C), 1247 (v. strong, sharp, Si--C) and 844 cm-1 (v. strong, broad, Si--C bending); mass spectrum (70 ev) m/e 391.

후처리

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. additionThe filtrate was diluted with 100 ml of ether
  4. washwashed with 200 ml each of 5% hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentrating the clear solution
  7. customyielded a solid mass which upon trituration with hexane

출처 및 근거

ORD 기록
ord-c83b308a3bc24421aaceda338e3e5340
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04465833

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