Indole → HCID 59238986, compound

HRID 2060971Notes

Reaction equation

HRID 2060971 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[CH2:56][CH2:55][CH:54]([NH:57]C(=O)OC(C)(C)C)[CH2:53][CH2:52]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][CH2:50][N:51]3[CH2:56][CH2:55][CH:54]([NH2:57])[CH2:53][CH2:52]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 22243834HCID 22243834, compoundHCID 67211699HCID 67211699, compound

Product 1

HCID 59238986HCID 59238986, 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 tert-butyl 1-(3-hydroxypropyl)piperidin-4-ylcarbamate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.70 (s, 2H), 8.33 (s, 1H), 8.07 (d, J=2.0 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.33 (dd, J=8.6, 2.2 Hz, 2H), 4.33 (t, J=5.4 Hz, 2H), 3.24-3.13 (m, 2H), 3.03-2.89 (m, 1H), 2.84 (t, J=6.0 Hz, 2H), 2.30-2.16 (m, 2H), 2.15-2.06 (m, 2H), 2.04-1.93 (m, 2H), 1.78-1.65 (m, 2H); MS (ESI) m/z 479.1 (M−H)−; MS (ESI) m/z 481.0 (M+H)+

Sources & evidence

ORD record
ord-2558d3370c0549ff949bf5cf34be693a
Source dataset
uspto-grants-2012_10
Patent number
US08278341B2

Reaction notes

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