Indole → HCID 59238883, compound

HRID 1949094Notes

Reaction equation

HRID 1949094 reaction equation
[NH:1]1[C:9]2[C:4](=CC=CC=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.O[C@H]1CCN(C(OC(C)(C)C)=O)C1>>[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][C@H:3]3[CH2:4][CH2:9][NH:1][CH2:2]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 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 67211699HCID 67211699, compound

Product 1

HCID 59238883HCID 59238883, 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)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.27 (br s, 2 H), 8.35 (s, 1 H), 8.07 (s, 2 H), 7.38-7.30 (m, 4 H), 5.09 (t, J=4.0 Hz, 1 H), 3.55-3.46 (m, 2 H), 3.29 (d, J=12.0 Hz, 1 H), 3.15 (td, J=10.0, 4.8 Hz, 1 H), 2.83 (dd, J=11.6, 3.6 Hz, 1 H), 2.38-2.28 (m, 1 H), 2.21-2.10 (m, 1 H); MS (ESI) m/z 408.2 (M−H)−; MS (ESI) m/z 410.1 (M+H)+

Sources & evidence

ORD record
ord-aa4a09a077d94832bec1dee701fa0419
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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