Indole → HCID 45136983, compound

HRID 1949113Notes

Reaction equation

N1C2C(=CC=CC=2)C=C1.C([N:17]1[C:29]2[C:28]([O:30][CH2:31][CH2:32][CH2:33]Br)=[C:27]3[N:35](C(OC(C)(C)C)=O)[C:36]4[CH:37]=[CH:38][C:39]([Br:42])=[CH:40][C:41]=4[C:26]3=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[C:21]([Br:50])[CH:22]=2)(OC(C)(C)C)=O.[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1>>[Br:50][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:29]1[C:28]([O:30][CH2:31][CH2:32][CH2:33][N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[C:27]3[NH:35][C:36]4[CH:37]=[CH:38][C:39]([Br:42])=[CH:40][C:41]=4[C:26]3=[CH:25][C:24]2=1

Participants

Reactant 3

HCID 798Indole

HCID 8083Morpholine

HCID 68650776HCID 68650776, compound

Product 1

HCID 45136983HCID 45136983, compound

Procedure

The title compound was prepared in a manner analogous to Example 70 except the starting indole is 5,7-diBOC-2,10-dibromo-6-(3-bromopropoxy)indolo[2,3-b]carbazole and the reagent is morpholine. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.28 (s, 2 H), 8.67 (s, 1 H), 8.28 (d, J=2.0 Hz, 2H), 7.51-7.40 (m, 4 H), 4.30 (t, J=6.6 Hz, 2 H), 3.56 (t, J=4.6 Hz, 4 H), 2.52 (t, J=7.2 Hz, 2 H), 2.44-2.32 (m, 4 H), 2.11-2.00 (m, 2 H); MS (ESI) m/z 556.0 (M−H)−

Sources & evidence

ORD record: ord-2fe2bca81e8645b2ab800039d8653300
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399502B2

Reaction notes

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