Indole → HCID 59238969, compound

HRID 1949095Notes

Reaction equation

HRID 1949095 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=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.C(N1CCC(CO)CC1)(OC(C)(C)C)=O>>[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][CH2:6][CH:5]3[CH2:3][CH2:2][NH:1][CH2:9][CH2:4]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 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 67211699HCID 67211699, compound

Product 1

HCID 59238969HCID 59238969, 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 N-Boc-4-piperidinemethanol. 1H-NMR (400 MHz, CD3OD) δ ppm 8.43 (s, 1H), 8.11 (d, J=2.0 Hz, 2 H), 7.43 (d, J=8.8 Hz, 2 H), 7.29 (dd, J=8.4, 2.0 Hz, 2 H), 4.16 (d, J=6.4 Hz, 2 H), 3.18-3.08 (m, 2 H), 2.70 (td, J=12.4, 2.4 Hz, 2 H), 2.22-2.10 (m, 1 H), 2.09-1.98 (m, 2 H), 1.50-1.38 (m, 2 H); MS (ESI) m/z 436.2 (M−H)−; MS (ESI) m/z 438.1 (M+H)+

Sources & evidence

ORD record
ord-01ead6f60cdf406ca6b5847ae960c82c
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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