5-Bromonicotinamide → HCID 16041930, 화합물

HRID 2218281노트

반응식

HRID 2218281 반응식
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:22][CH2:21][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27](B5OC(C)(C)C(C)(C)O5)[CH:28]=4)[O:23]3)[CH2:19][CH2:18]2)=[O:16])[CH:4]=1.Br[C:43]1[CH:44]=[N:45][CH:46]=[C:47]([CH:51]=1)[C:48]([NH2:50])=[O:49].O1CCOCC1>C(Cl)(Cl)Cl.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>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:18][CH2:19][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:43]5[CH:44]=[N:45][CH:46]=[C:47]([CH:51]=5)[C:48]([NH2:50])=[O:49])[CH:28]=4)[O:23]3)[CH2:21][CH2:22]2)=[O:16])[CH:4]=1

참가 물질

6

반응물 3

HCID 18085-BromonicotinamideHCID 312751,4-DioxaneHCID 57700063HCID 57700063, 화합물

생성물 1

HCID 16041930HCID 16041930, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6212Chloroform용매

실험 절차

350 mg of 1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4′-piperidin]-4-one, 151 mg of 5-bromonicotinamide, 72.5 mg of Pd(PPh3)4 and 1.4 mL of 2M Na2CO3aq were heated with 1,4-dioxane at 100° C. and stirred for 21 hours. The reaction solution was diluted with CHCl3, filtered through Celite, and the filtrate was dried with magnesium sulfate and concentrated. The residue was purified through silica gel thin-layer chromatography (CHCl3/MeOH=9/1) to obtain the intended compound. 1H-NMR (400 MHz, CDCl3) δ: 8.90-9.00 (2H, m), 8.36 (1H, s), 8.15 (1H, s), 7.70-7.80 (2H, m), 7.40-7.55 (1H, m), 7.19 (1H, s), 7.17 (1H, d, J=8.8 Hz), 7.09 (1H, d, J=7.8 Hz), 6.3-6.5 (1H, br), 5.7-6.1 (1H, br), 4.50-4.60 (1H, m), 4.10-4.15 (1H, m), 4.08 (3H, s), 4.03 (3H, s), 3.55-3.70 (1H, m), 3.35-3.50 (1H, m), 2.88 (1H, d, J=16.6 Hz), 2.82 (1H, d, J=16.6 Hz), 2.20-2.30 (1H, m), 2.05-2.15 (1H, m), 1.80-2.05 (2H, m). MS [M+H]+=553.

후처리

  1. filtrationfiltered through Celite
  2. dry with materialthe filtrate was dried with magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified through silica gel thin-layer chromatography (CHCl3/MeOH=9/1)
  5. customto obtain the intended compound

출처 및 근거

ORD 기록
ord-1643f036b2af482dacfc275dc6ee0cdd
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07410976B2

반응 노트

불러오는 중…