Sodium → 3-Bromo-6-chloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1888401ノート

反応式

HRID 1888401 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[N:12]=[CH:11][C:10]=2[NH2:16])[C:5](F)=[N:6][CH:7]=1.[Na].C[Si]([NH-])(C)C>C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[NH:16][C:10]3[CH:11]=[N:12][C:13]([Cl:15])=[CH:14][C:9]=3[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 5360545SodiumHCID 53627528(Trimethylsilyl)amideHCID 582665005-Bromo-6'-chloro-2-fluoro-[3,4']bipyridinyl-3'-ylamine

生成物 1

HCID 582664913-Bromo-6-chloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 5-bromo-6′-chloro-2-fluoro-[3,4′]-bipyridinyl-3′-ylamine (2.21 g, 7.32 mmol) in THF (124 mL) was added dropwise over 10 minutes to sodium his-(trimethylsilyl)amide ON solution in THF, 14.6 mL, 14.6 mmol). The reaction mixture was stirred for 1 h at ambient temperature and then quenched by the addition of water (2 mL). The resultant brown solution was partitioned between ethyl acetate (75 mL) and brine (50 mL). An off-white solid precipitated and was collected by filtration to afford the title compound as a grey solid (1.01 g, 49%). 1H NMR (DMSO-D6, 300 MHz): 9.01 (d, J=2.3 Hz, 1H), 8.73 (s, 1H), 8.70 (d, J=2.3 Hz, 1H), 8.35 (s, 1H). LCMS (Method B): RT=3.33 min, M+H+=284.

後処理

  1. customquenched by the addition of water (2 mL)
  2. customThe resultant brown solution was partitioned between ethyl acetate (75 mL) and brine (50 mL)
  3. customAn off-white solid precipitated
  4. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-ce5431f441924c3dacdd6d03ec322226
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

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