Potassium Carbonate → 5-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)oxazole

HRID 588153Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:40]([CH2:42]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:41]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:42]=[N:40][CH:41]=2)[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (Intermediate 11B, 200 mg, 0.441 mmol), potassium carbonate (63.9 mg, 0.463 mmol) and 1-(isocyanomethylsulfonyl)-4-methylbenzene (90 mg, 0.463 mmol) were taken up in MeOH (1.8 ml) and were stirred at 65° C. overnight. The mixture was concentrated in vacuo while loading onto silica gel and purificied by MPLC 0-25% EtOAc/DCM to give 5-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)oxazole (54B). MS: [M+H]+ m/z 493.

Workup

concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-26752f17771549b4b9763b2bc92ae87f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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