Trifluoroacetic acid → HCID 69231942, compound

HRID 2118137Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[C:10]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[CH:23]3)=[C:9]1[C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:10]2[C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[CH:23]2

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 69229694HCID 69229694, compound

Product 1

HCID 69231942HCID 69231942, compound

Procedure

Ethyl 5-amino-1-benzyl-1H,1′H-3,5′-biindole-2-carboxylate was prepared from ethyl 1-benzyl-5-nitro-1H,1′H-3,5′-biindole-2-carboxylate followed the procedure of Example 1 Step 2 as a white solid: 1H NMR (DMSO-d6) δ 0.89 (t, J=7.1 Hz, 3H, 4.06 (q, J=7.1 Hz, 2H, 5.81 (s, 2H, 6.47 (t, J=2.0 Hz, 1H, 7.08 (d, J=7.1 Hz, 2H, 7.10-7.50 (m, 8H), 7.58 (s, 1H, 7.70 (d, J=8.9 Hz, 1H, 9.28 (br s, 2H, 11.18 (s, 1H; MS (ESI) m/z 410 (MH+); HRMS calcd for C26H24N3O2: 410.1867 found (ESI+): 410.1858; Anal. calcd for C26H23N3O2.1.0 TFA: C, 64.24; H, 4.62; N, 8.03. Found: C, 63.85; H, 4.77; N, 7.91.

Sources & evidence

ORD record: ord-e71b6a0b02304ea89fc04ab5cd67ee49
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442805B2

Reaction notes

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