HCID 68932330, compound → HCID 73320859, compound

HRID 2191247Notes

Reaction equation

O=C1C(=[C:11]([C:14]#[N:15])[C:12]#[N:13])C2C(=CC=C(S(N3CCCC3COC3C=CC=CC=3)(=O)=O)C=2)N1.[Br:32][C:33]1[CH:66]=[CH:65][C:36]([CH2:37][N:38]2[C:46]3[C:41](=[CH:42][C:43]([S:47]([N:50]4[CH2:54][CH2:53][CH2:52][CH:51]4[CH2:55][O:56][C:57]4[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=4)(=[O:49])=[O:48])=[CH:44][CH:45]=3)[C:40](=O)[C:39]2=[O:64])=[CH:35][CH:34]=1>>[Br:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:37][N:38]2[C:46]3[C:41](=[CH:42][C:43]([S:47]([N:50]4[CH2:54][CH2:53][CH2:52][CH:51]4[CH2:55][O:56][C:57]4[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=4)(=[O:49])=[O:48])=[CH:44][CH:45]=3)[C:40](=[C:11]([C:14]#[N:15])[C:12]#[N:13])[C:39]2=[O:64])=[CH:65][CH:66]=1

Participants

Reactant 2

HCID 68932330HCID 68932330, compound

HCID 73320783HCID 73320783, compound

Product 1

HCID 73320859HCID 73320859, compoundYield 45%

Procedure

2-{1-(4-Bromo-benzyl)-2-oxo-5-[2-(pyndine-3-yloxymethyl)-pyrrolidine-1-sulfonyl]-1,2-dihydro-indol-3-yl-idene}-malononitrile (30c) was prepared according to the same procedure for compound 26 except using 28c, to afford 16 mg (45%) of 30c as a purple solid, mp 232.3° C. (decomp). 1H NMR (300 MHz, CDCl3) δ 8.50 (s, 1H), 8.21 (m, 1H), 8.16 (s, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.20 (m, 4H), 6.84 (d, J=8.7 Hz, 1H), 4.89 (m, 2H), 4.20 (m, 1H), 4.02 (m, 2H), 2.05-1.78 (m, 4H).

Workup

custom2-{1-(4-Bromo-benzyl)-2-oxo-5-[2-(pyndine-3-yloxymethyl)-pyrrolidine-1-sulfonyl]-1,2-dihydro-indol-3-yl-idene}-malononitrile (30c) was prepared

Sources & evidence

ORD record: ord-331b8d93b40b4b47b808b89e0e8fc28f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329686B2

Reaction notes

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