Pyridine → HCID 10984336, compound

HRID 989779Notes

Reaction equation

[N:1]1([CH2:10][C:11]2[N:16]=[C:15]([CH2:17][N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])[CH:14]=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:29](Cl)(=[O:33])[C:30](Cl)=[O:31].[OH:35][N:36]1[C:40](=[O:41])[CH2:39][CH2:38][C:37]1=[O:42].N1C=CC=CC=1>ClCCl>[O:42]=[C:37]1[CH2:38][CH2:39][C:40](=[O:41])[N:36]1[O:35][C:29](=[O:33])[C:30]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH2:17][N:18]3[C:19](=[O:28])[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]3=[O:27])[N:16]=2)[CH:2]=1)=[O:31]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(6-Indol-1-ylmethyl-pyridin-2-ylmethyl)-isoindole-1,3-dione (2.70 g, 7.35 mmol) was dissolved in dichloromethane (50 ml) and cooled to 0° C. Oxalylchloride (0.63 ml, 7.35 mmol) was added and the reaction kept at 0° C. for 30 minutes before the addition of N-hydroxysuccinimide (0.85 g, 7.35 mmol) followed by careful addition of pyridine (1.19 ml, 14.7 mmol). The reaction was kept at 0° C. for 30 minutes before it was allowed to slowly regain room temperature during 3 hours and then washed with water (40 ml) and brine (2×50 ml). The organic layer was dried over MgSO4 followed by removal of the solvent in vacuo to obtain the sub-title product (3.34 g, 85%).

Workup

waitwas allowed to slowly regain room temperature during 3 hours
washwashed with water (40 ml) and brine (2×50 ml)
dry with materialThe organic layer was dried over MgSO4
customfollowed by removal of the solvent in vacuo

Sources & evidence

ORD record: ord-6014673dfcd9414987f1d05c23e3c229
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458792B1

Reaction notes

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