Dimethylformamide → HCID 21102146, 화합물

HRID 2250245노트

반응식

HRID 2250245 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH2:5]2.[CH3:19][N:20](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:12]=[C:7]1[N:6]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:19]#[N:20])[CH:3]=2)[NH:8]1

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 21102206HCID 21102206, 화합물

생성물 1

HCID 21102146HCID 21102146, 화합물수율 38%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
90 °C

실험 절차

6-Bromo-3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (0.16 g, 0. 52 mmol), zinc cyanide (37 mg, 0.31 mmol) and tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) were combined in dimethylformamide (4 mL). The reaction flask was connected to high vacuum and degassed (3×) by a freeze-thawing method, before being heated at 90° C. with stirring under nitrogen for 1 h. After cooling to room temperature, the solution was evaporated in vacuo and the crude mixture purified by preparative HPLC to afford 50 mg (38%) of the desired nitrile. 1H-NMR (CD3OD) δ 1.99 (m, 2H), 2.08-2.23 (m, 2H), 3.15 (m, 2H), 3.50 (bs, 1H), 3.55 (bs, 1H), 4.40 (m, 1H), 4.47 (s, 2H), 6.93 (d, J=8.1, 1H), 4.10 (m, 2H). Mass spec.: 257.13 (MH)+.

후처리

  1. customdegassed (3×) by a freeze-thawing method
  2. temperatureAfter cooling to room temperature
  3. customthe solution was evaporated in vacuo
  4. customthe crude mixture purified by preparative HPLC

출처 및 근거

ORD 기록
ord-bd5443ac78e64ba6889b0853e4d8550b
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314883B2

반응 노트

불러오는 중…