5-Aminoindole → 6-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine

HRID 85032ノート

反応式

HRID 85032 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C(N(C(C)C)CC)(C)C>CCO>[Br:8][C:6]1[N:7]=[C:2]([NH:19][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[NH:10][CH:11]=[CH:12]3)[C:3]([NH2:9])=[N:4][CH:5]=1

参加物

5

反応物 3

HCID 788675-AminoindoleHCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazine

生成物 1

HCID 727136316-bromo-N2-(1H-indol-5-yl)pyrazine-2,3-diamine収率 42%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a stirred suspension of 3,5-dibromopyrazin-2-amine (3.48 g, 13.7 mmol) and 1H-indol-5-amine (2.00 g, 15.0 mmol) in EtOH (3.5 mL) was added diisopropylethylamine [DIEA](2.60 mL, 15.0 mmol). The resulting mixture was stirred for 48 hr at 80° C., after which it was partitioned between EtOAc and H2O. The organic layer was separated, after which it was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo to yield a residue that was purified via silica gel chromatography eluting with 1:1 EtOAc:hexanes to yield the title compound (1.75 g, 42%) as a red/brown solid. 1H NMR (DMSO-d6, 300 MHz): δ 10.98 (s, 1H), 8.22 (s, 1H), 7.83 (s, 1H), 7.31-7.28 (m, 3H), 7.19 (d, J=8.7 Hz, 1H), 6.43 (s, 2H), 6.36 (s, 1H); HPLC retention time: 2.07 minutes; MS ESI (m/z): 304.2/306.2 (M+1)+, calc. 303.

後処理

  1. customafter which it was partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. washafter which it was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield a residue that
  8. customwas purified via silica gel chromatography
  9. washeluting with 1:1 EtOAc

出典と根拠

ORDレコード
ord-f7905f2ad51b403c8028a94762e0c523
出典データセット
uspto-grants-2014_09
特許番号
US08846909B2

反応ノート

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