Indole → HCID 59238951, compound

HRID 1949103Notes

Reaction equation

HRID 1949103 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]([Br: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]([Br:46])[CH:22]=2)(OC(C)(C)C)=O.O[CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>>[Br: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][N:50]3[CH2:55][CH2:54][O:53][CH2:52][CH2:51]3)=[C:29]3[NH:17][C:18]4[CH:19]=[CH:20][C:21]([Br:46])=[CH:22][C:23]=4[C:24]3=[CH:25][C:26]2=1

Participants

4

Reactant 3

HCID 798IndoleHCID 611632-MorpholinoethanolHCID 16749420HCID 16749420, compound

Product 1

HCID 59238951HCID 59238951, compound

Procedure

The title compound was prepared in a manner analogous to Example 28 except the starting indole is 5,7-diBOC-2,10-dibromo-6-hydroxyindolo[2,3-b]carbazole and the reagent is 4-(2-Hydroxyethyl)morpholine. 1H-NMR (400 MHz, CD3OD) δ ppm 8.44 (s, 1 H), 8.25 (d, J=2.0 Hz, 2 H), 7.42 (dd, J=8.4, 1.6 Hz, 2 H), 7.41 (d, J=2.0 Hz, 2 H), 4.42 (t, J=5.2 Hz, 2 H), 3.81 (t, J=4.8 Hz, 4H), 2.87 (t, J=5.2 Hz, 2 H), 2.70-2.60 (m, 4 H); MS (ESI) m/z 542.1 (M−H)−

Sources & evidence

ORD record
ord-05bbdd83acff44ec8ae006521ecfc6ce
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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