Indole → HCID 59239027, compound

HRID 1949102Notes

Reaction equation

HRID 1949102 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.[CH3:47][N:48]([CH3:56])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]O>>[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][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][N:48]([CH3:56])[CH3:47])=[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 746236-Dimethylaminohexan-1-olHCID 67211699HCID 67211699, compound

Product 1

HCID 59239027HCID 59239027, 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 6-dimethylamino-1-hexanol. 1H-NMR (400 MHz, CDCl3) δ ppm 8.35 (s, 1 H), 8.20 (s, 2 H), 8.08 (s, 2 H), 7.41-7.32 (m, 4 H), 4.28 (t, J=6.4 Hz, 2 H), 2.31 (t, J=7.2 Hz, 2 H), 2.23 (s, 6 H), 2.00-1.90 (m, 2 H), 1.65-1.42 (m, 6 H); MS (ESI) m/z 466.2 (M−H)−; MS (ESI) m/z 468.1 (M+H)+

Sources & evidence

ORD record
ord-d4ed966a5da5417a8621c652fb4d6b82
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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