HCID 67211749, compound → HCID 59239024, compound

HRID 1949111Notes

Reaction equation

HRID 1949111 reaction equation
C([N:8]1[C:20]2[C:19]([O:21][CH2:22][CH2:23][CH2:24]Br)=[C:18]3[N:26](C(OC(C)(C)C)=O)[C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][C:32]=4[C:17]3=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([F:41])[CH:13]=2)(OC(C)(C)C)=O.[OH:42][C:43]1[CH2:47][CH2:46][NH:45][CH:44]=1>>[F:41][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:20]1[C:19]([O:21][CH2:22][CH2:23][CH2:24][N:45]3[CH2:46][CH2:47][CH:43]([OH:42])[CH2:44]3)=[C:18]3[NH:26][C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][C:32]=4[C:17]3=[CH:16][C:15]2=1

Participants

3

Reactant 2

HCID 67211749HCID 67211749, compoundHCID 67212247HCID 67212247, compound

Product 1

HCID 59239024HCID 59239024, compoundYield 90%

Procedure

The title compound was prepared in a manner analogous to Example 70 except the staring material is 5,7-diBOC-2,10-difluoro-6-(3-bromopropoxy)indolo[2,3-b]carbazole and the reagent is 3-hydroxypyrroline. The reaction can be completed at room temperature overnight. 1H-NMR (400 MHz, CDCl3) δ ppm 9.57 (br s, 2 H), 8.27 (s, 1 H), 7.71 (dd, J=9.2, 2.4 Hz, 2 H), 7.33 (dd, J=8.8, 4.0 Hz, 2H), 7.03 (td, J=8.8, 2.4 Hz, 2 H), 4.67-4.59 (m, 1 H), 4.40-4.26 (m, 2 H), 3.80 (t, J=5.6 Hz, 1 H), 3.15-3.00 (m, 2 H), 2.96-2.80 (m, 3 H), 2.73-2.61 (m, 1 H), 2.38-2.26 (m, 1 H), 2.12-1.93 (m, 2 H), 1.79-1.70 (m, 1 H); MS (ESI) m/z 434.2 (M−H)−; MS (ESI) m/z 436.1 (M+H)+

Workup

  1. customThe reaction

Sources & evidence

ORD record
ord-614a16a3a25843e6a5d45d904e7884a8
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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