7-Chlorothieno[3,2-b]pyridine → tert-Butyl 2-(4-(7-chlorothieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(methyl)carbamate

HRID 1261270Notes

Reaction equation

HRID 1261270 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.ClC1C=CN=C2C=C(C3N=CN(C)C=3)SC=12.I[C:28]1[CH:29]=[N:30][N:31]([CH2:33][CH2:34][N:35]([CH3:43])[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:32]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:28]3[CH:29]=[N:30][N:31]([CH2:33][CH2:34][N:35]([CH3:43])[C:36](=[O:42])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[CH:32]=3)[S:10][C:3]=12

Participants

4

Reactant 3

HCID 112752517-Chlorothieno[3,2-b]pyridineHCID 594245247-Chloro-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridineHCID 59424644tert-butyl 2-(4-iodo-1H-pyrazol-1-yl)ethyl(methyl)carbamate

Product 1

HCID 59457667tert-Butyl 2-(4-(7-chlorothieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(methyl)carbamateYield 75%

Procedure

Starting from the chloride 2 and following the procedure described above for the synthesis of 175 (scheme 35, example 138), but replacing 4-iodo-1-methyl-1H-imidazole with tert-butyl 2-(4-iodo-1H-pyrazol-1-yl)ethyl(methyl)carbamate, title compound 180 was obtained in 75% yield. LRMS (M+1) 393.1 (100%).

Sources & evidence

ORD record
ord-cbf5dada92b641f2a36a2a826f83516b
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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