Potassium Iodide → HCID 21186279, compound

HRID 1384196Notes

Reaction equation

C(OC([N:8]([C:28]1[C:33]([O:34][CH3:35])=[N:32][C:31]([CH3:36])=[CH:30][N:29]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=O)C(C)C.[I-].[K+].C(OC1C=CC(B(O)O)=CC=1)(C)C>>[CH:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([S:9]([NH:8][C:28]3[C:33]([O:34][CH3:35])=[N:32][C:31]([CH3:36])=[CH:30][N:29]=3)(=[O:11])=[O:10])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:19][CH:20]=1)([CH3:27])[CH3:26]

Participants

Reactant 3

HCID 4875Potassium Iodide

HCID 36987264-Isopropoxybenzeneboronic acid

HCID 21186333HCID 21186333, compound

Product 1

HCID 21186279HCID 21186279, compound

Procedure

1H NMR (CDCl3): 1.40 (d, 6H), 2.3 (s, 3H), 3.8 (s, 3H), 4.6 (m, 1H), 6.7 (br s, 1H), 6.9 (d, 2H), 7.2-7.35 (m, 3H), 7.5 (dd, 1H), 8.7 (dd, 1H), 8.8 (dd, 1H); mass spectrum (+ve ESP): 415 (M+H)+; starting from N-isobutoxycarbonyl-2-(4-isopropoxyphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide; 1H NMR (CDCl3): 0.7 (d, 6H), 1.40 (d, 6H), 1.7 (m, 1H), 2.5 (s, 3H), 3.8 (d, 3H), 4.0 (s, 3H), 4.6 (m, 1H), 6.9 (d, 2H), 7.45 (dd, 1H), 7.6 (d, 2H), 7.9 (s, 1H), 8.8 (dd, 1H), 8.95 (dd, 1H); mass spectrum (+ve ESP): 515 (M+H)+; itself obtained using an analogous procedure to that described in Example 1, part (iii) but with the addition of potassium iodide (1 molar equivalent) and using 4-isopropoxyphenylboronic acid which was prepared as described in European Patent Application, publication no. 569193.

Workup

customitself obtained
customwas prepared

Sources & evidence

ORD record: ord-95176b54b1de4c8480da6130002a1b34
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258817B1

Reaction notes

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