Indole → HCID 59238876, compound

HRID 1949114Notes

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][CH2:34]Br)=[C:27]3[N:36](C(OC(C)(C)C)=O)[C:37]4[CH:38]=[CH:39][C:40]([Br:43])=[CH:41][C:42]=4[C:26]3=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[C:21]([Br:51])[CH:22]=2)(OC(C)(C)C)=O.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>>[Br:43][C:40]1[CH:41]=[C:42]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:27]1[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[C:29]3[NH:17][C:18]4[CH:19]=[CH:20][C:21]([Br:51])=[CH:22][C:23]=4[C:24]3=[CH:25][C:26]2=1

Participants

Reactant 3

HCID 798Indole

HCID 8083Morpholine

HCID 68651246HCID 68651246, compound

Product 1

HCID 59238876HCID 59238876, 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-(4-bromobutoxy)indolo[2,3-b]carbazole and the reagent is morpholine. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.22 (s, 2 H), 8.64 (s, 1 H), 8.25 (d, J=1.6 Hz, 2H), 7.44 (dd, J=8.4, 2.0 Hz, 2 H), 7.41 (d, J=8.4 Hz, 2 H), 4.26 (t, J=6.8 Hz, 2 H), 3.57-3.40 (m, 6 H), 2.32-2.18 (m, 4 H), 1.92-1.80 (m, 2 H), 1.65-1.50 (m, 2 H); MS (ESI) m/z 570.0 (M−H)−

Sources & evidence

ORD record: ord-da7437927c96499eabdb8fec4d520dfe
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399502B2

Reaction notes

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