Hydrochloric Acid → HCID 86676742, compound

HRID 2199329Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([N+]([O-])=O)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[C:34]2[C:39]([OH:41])=[O:40].Cl>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([O:28][C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH:31]=[CH:32][CH:33]=[C:34]3[C:39]([OH:41])=[O:40])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (400 mg, 1.22 mmol) in DMSO (4 mL) were added K2CO3 (507 mg, 3.67 mmol) and 5-hydroxy-1-naphthoic acid (230 mg, 1.22 mmol). The reaction mixture was stirred for overnight at 100° C. after which, It was cooled to room temperature. To the reaction mixture was added 1N HCl solution to reach pH=5. The produced solid was filtered and dried nitrogen gas flow. The title compound (380 mg, 66% yield) was used next reaction without further purification. MS m/z: 469 [M+1].

Workup

temperaturewas cooled to room temperature
filtrationThe produced solid was filtered

Sources & evidence

ORD record: ord-3daeb7a95c174d699dfb76dfce09d5dc
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09358231B2

Reaction notes

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