Indole → HCID 59238891, compound

HRID 1949096Notes

Reaction equation

HRID 1949096 reaction equation
[NH:1]1[C:9]2[C:4](=CC=C[CH:8]=2)[CH:3]=[CH:2]1.C([N:17]1[C:29]2[C:28]([OH:30])=[C:27]3[N:31](C(OC(C)(C)C)=O)[C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][C:37]=4[C:26]3=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[C:21]([Cl:46])[CH:22]=2)(OC(C)(C)C)=O.C(OC(N1CCC[C@H]1CO)=O)(C)(C)C>>[Cl:38][C:35]1[CH:36]=[C:37]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:27]1[C:28]([O:30][CH2:8][C@@H:9]3[CH2:4][CH2:3][CH2:2][NH:1]3)=[C:29]3[NH:17][C:18]4[CH:19]=[CH:20][C:21]([Cl:46])=[CH:22][C:23]=4[C:24]3=[CH:25][C:26]2=1

Participants

4

Reactant 3

HCID 798IndoleHCID 643448(S)-(-)-N-Boc-prolinolHCID 67211699HCID 67211699, compound

Product 1

HCID 59238891HCID 59238891, compound

Procedure

The title compound was prepared in a manner analogous to Example 28 except the starting indole is 5,7-diBOC-2,10-dichloro-6-hydroxyindolo[2,3-b]carbazole and the reagent is (S)-(+)-1-(tert-butoxycarbonyl)-2-pyrrolidinemethanol. 1H-NMR (400 MHz, CD3OD) δ ppm 8.46 (s, 1 H), 8.11 (d, J=2.4 Hz, 2 H), 7.41 (d, J=8.4 Hz, 2 H), 7.30 (dd, J=8.4, 2.4 Hz, 2 H), 4.33 (dd, J=10.0, 3.2 Hz, 1 H), 4.11 (dd, J=10.0, 8.4 Hz, 1 H), 3.91-3.82 (m, 1 H), 3.16 (t, J=7.2 Hz, 2 H), 2.16-2.05 (m, 1 H), 2.03-1.84 (m, 2 H), 1.72-1.62 (m, 1 H); MS (ESI) m/z 422.2 (M−H)−; MS (ESI) m/z 424.0 (M+H)+

Sources & evidence

ORD record
ord-396ab488ae48400abdb362d55f70508b
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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