Indole → HCID 59238970, compound

HRID 1949101Notes

Reaction equation

HRID 1949101 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][CH2:50][N:51]1[CH2:55][CH2:54][C@H:53]([NH:56]C(=O)OC(C)(C)C)[CH2:52]1>>[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][CH2:48][CH2:49][CH2:50][N:51]3[CH2:55][CH2:54][C@H:53]([NH2:56])[CH2:52]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 67211699HCID 67211699, compoundHCID 70944919HCID 70944919, compound

Product 1

HCID 59238970HCID 59238970, 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-(3-hydroxypropyl)pyrrolidin-3-ylcarbamate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.92 (s, 2 H), 8.34 (s, 1H), 8.08 (s, 2 H), 7.39-7.29 (m, 4 H), 4.42-4.31 (m, 2 H), 3.90-3.79 (m, 1 H), 3.26 (dd, J=9.8, 6.6 Hz, 1H), 3.09-2.99 (m, 2 H), 2.98-2.86 (m, 2 H), 2.50-2.36 (m, 2 H), 2.15-2.05 (m, 2 H), 1.82-1.71 (m, 1 H); MS (ESI) m/z 465.1 (M−H)−; MS (ESI) m/z 467.0 (M+H)+

Sources & evidence

ORD record
ord-3be4c132b0bb4fc7aef4113d5c0d9258
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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