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

HRID 712548노트

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HRID 712548 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ee2d95e270f54bf1b0e3f5004d6588e6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181247B2

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