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

HRID 333156Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-439dd1c39cb040218845473713ab8456
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877772B2

Reaction notes

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