HCID 68932334, compound → HCID 73320858, compound

HRID 2191245Notes

Reaction equation

[O:1]=[C:2]1[C:10](=[C:11]([C:14]#[N:15])[C:12]#[N:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:16]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:18])=[O:17])[CH:8]=2)[NH:3]1.[Br:32][C:33]1[CH:66]=[CH:65][C:36]([CH2:37]N2C3C(=CC(S(N4CCCC4COC4C=CC=CC=4)(=O)=O)=CC=3)C(=O)C2=O)=[CH:35][CH:34]=1>>[Br:32][C:33]1[CH:66]=[CH:65][C:36]([CH2:37][N:3]2[C:4]3[C:9](=[CH:8][C:7]([S:16]([N:19]4[CH2:23][CH2:22][CH2:21][CH:20]4[CH2:24][O:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)(=[O:17])=[O:18])=[CH:6][CH:5]=3)[C:10](=[C:11]([C:12]#[N:13])[C:14]#[N:15])[C:2]2=[O:1])=[CH:35][CH:34]=1

Participants

Reactant 2

HCID 68932334HCID 68932334, compound

HCID 73320783HCID 73320783, compound

Product 1

HCID 73320858HCID 73320858, compoundYield 86%

Procedure

2-[1-(4-Bromo-benzyl)-2-oxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1,2-dihydro-indol-3-yl-idene]-malononitrile (27d) was prepared according to the same procedure for compound 26 except using 25d, to afford 52 mg (86%) of 27d as a purple solid, mp 237.0° C. (decomp). 1H NMR (300 MHz, CDCl3) δ 8.46 (s, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.20-7.13 (m, 4H), 6.90 (t, J=7.5 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 6.68 (d, J=7.8 Hz, 2H), 4.84 (m, 2H), 4.06 (m, 2H), 3.97 (m, 1H), 3.46 (m, 2H), 2.08-1.86 (m, 4H).

Workup

custom2-[1-(4-Bromo-benzyl)-2-oxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1,2-dihydro-indol-3-yl-idene]-malononitrile (27d) was prepared

Sources & evidence

ORD record: ord-cab1c1e732cf414aac0a27225372385e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329686B2

Reaction notes

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