5-Indolylboronic acid → HCID 69229694, compound

HRID 2118136Notes

Reaction equation

HRID 2118136 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10](Br)=[C:9]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[C:34]2[C:29](=[CH:30][C:31](B(O)O)=[CH:32][CH:33]=2)[CH:28]=[CH:27]1>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([C:31]2[CH:30]=[C:29]3[C:34](=[CH:33][CH:32]=2)[NH:26][CH:27]=[CH:28]3)=[C:9]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343615-Indolylboronic acidHCID 69231351HCID 69231351, compound

Product 1

HCID 69229694HCID 69229694, compound

Procedure

Ethyl 1-benzyl-5-nitro-1H,1′H-3,5′-biindole-2-carboxylate was prepared from ethyl 1-benzyl-3-bromo-5-nitro-1H-indole-2-carboxylate and indole-5-boronic acid followed the procedure of Example 17 Step 2 as a yellowish solid: 1H NMR (DMSO-d6) δ 0.90 (t, J=7.1 Hz, 3H, 4.10 (q, J=7.1 Hz, 2H, 5.89 (s, 2H, 6.52 (t, J=1.1 Hz, 1H, 7.11 (d, J=8.4 Hz, 2H, 7.20 (dd, J=8.3, 1.7 Hz, 1H, 7.22-7.35 (m, 3H, 7.42 (t, J=2.7 Hz, 1H, 7.52 (d, J=8.4 Hz, 1H, 7.66 (s, 1H, 7.90 (d, J=9.3 Hz, 1H, 8.21 (dd, J=9.2, 2.2 Hz, 1H, 8.40 (d, J=2.2 Hz, 1H, 11.23 (s, 1H; MS (ESI) m/z 440 (MH+); MS (ESI) m/z 438 [M-H]−; HRMS calcd for C26H22N3O4: 440.1608; found (ESI+): 440.1596; Anal. calcd for C26H21N3O4.0.25H2O: C, 70.34; H, 4.88; N, 9.47. Found: C, 70.23; H, 4.89; N, 9.58.

Sources & evidence

ORD record
ord-72ee2c2f19114b4293841d43f8225de5
Source dataset
uspto-grants-2008_10
Patent number
US07442805B2

Reaction notes

Loading…