Indole → HCID 59239026, compound

HRID 1949100Notes

Reaction equation

HRID 1949100 reaction equation
N1C2C(=CC=CC=2)C=C1.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[CH2:48][CH2:49][N:50]1[CH2:54][CH2:53][C@H:52]([NH:55]C(=O)OC(C)(C)C)[CH2:51]1>>[Cl:46][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:29]1[C:28]([O:30][CH2:48][CH2:49][N:50]3[CH2:54][CH2:53][C@H:52]([NH2:55])[CH2:51]3)=[C:27]3[NH:31][C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][C:37]=4[C:26]3=[CH:25][C:24]2=1

Participants

4

Reactant 3

HCID 798IndoleHCID 66565985HCID 66565985, compoundHCID 67211699HCID 67211699, compound

Product 1

HCID 59239026HCID 59239026, 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 1-(2-hydroxyethyl)pyrrolidin-3-ylcarbamate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.91 (s, 2 H), 8.37 (s, 1H), 8.08 (d, J=1.6 Hz, 2 H), 7.40-7.29 (m, 4 H), 4.43-4.33 (m, 2 H), 3.88-3.78 (m, 1 H), 3.09-2.96 (m, 2H), 2.95-2.74 (3 H), 2.61 (dd, J=9.6, 5.0 Hz, 1 H), 2.43-2.31 (m, 1 H), 1.79-1.68 (m, 1 H); MS (ESI) m/z 451.1 (M−H)−; MS (ESI) m/z 453.0 (M+H)+

Sources & evidence

ORD record
ord-3b18dd941b66407b945b22d562dcd4e6
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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