Stannanecarbonitrile, tributyl- → 4-fluoro-3-[2-oxo-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]acetyl]-1H-pyrrolo[2,3-c]pyridine-7-carbonitrile

HRID 1157300ノート

反応式

HRID 1157300 の反応式
Br[C:2]1[N:3]=[CH:4][C:5]([F:32])=[C:6]2[C:10]([C:11](=[O:31])[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:7]=12.C([Sn]([C:46]#[N:47])(CCCC)CCCC)CCC>O1CCOCC1.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>[F:32][C:5]1[CH:4]=[N:3][C:2]([C:46]#[N:47])=[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:31])[C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([C:20]4[N:24]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:23]=[N:22][N:21]=4)[CH2:18][CH2:19]3)[C:6]=12

参加物

5

反応物 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 595113051-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione

生成物 1

HCID 497701594-fluoro-3-[2-oxo-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]acetyl]-1H-pyrrolo[2,3-c]pyridine-7-carbonitrile収率 31.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a sealable flask containing 1-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (0.10 g, 0.20 mmol) in 1,4-dioxane (5 mL) was added tributyltin cyanide (0.07 g, 0.22 mmol) followed by Pd(PPh3)4 (0.07 g, 0.06 mmol). The mixture was flushed with N2, and the tube was sealed and heated to 100° C. After 16h of heating, the mixture was cooled to rt, and the solvent was removed in vacuo. The residue was dissolved in DMF and was filtered through a pad of celite to remove any remaining solids. The DMF solution was purified by prep HPLC to give the title compound as an off-white solid (0.028 g). LCMS: m/e 446.2 (M+H)+, ret time 1.81 min (method 2). 1H NMR (500 MHz, DMSO-D6) δ ppm 14.06 (s, 1 H) 8.66 (s, 1 H) 8.50 (d, J=2.14 Hz, 1 H) 7.56-7.70 (m, 5 H) 3.67-3.72 (m, 2 H) 3.33-3.50 (m, 4 H) 3.13-3.17 (m, 2 H).

後処理

  1. customThe mixture was flushed with N2
  2. customthe tube was sealed
  3. temperatureAfter 16h of heating
  4. temperaturethe mixture was cooled to rt
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in DMF
  7. filtrationwas filtered through a pad of celite
  8. customto remove any remaining solids
  9. customThe DMF solution was purified by prep HPLC

出典と根拠

ORDレコード
ord-840aa8d704b9404db59a871aded3f03c
出典データセット
uspto-grants-2010_10
特許番号
US07807671B2

反応ノート

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