3-Bromopyrazolo(1,5-a)pyrimidine → (R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate

HRID 2018047Notes

Reaction equation

HRID 2018047 reaction equation
Br[c:1]1[c:9]([n:4]2[n:3][cH:2]1)[n:8][cH:7][cH:6][cH:5]2.[CH3:10][c:11]1[c:16]([N:17]([C:31]([c:33]2[cH:38][cH:37][c:36](B3OC(C)(C)C(C)(C)O3)[cH:35][cH:34]2)=[O:32])[C@H:18]4[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21][CH2:20][CH2:19]4)[n:15][cH:14][cH:13][cH:12]1>>[CH3:10][c:11]1[c:16]([N:17]([C:31]([c:33]2[cH:38][cH:37][c:36]([c:1]3[c:9]([n:4]4[n:3][cH:2]3)[n:8][cH:7][cH:6][cH:5]4)[cH:35][cH:34]2)=[O:32])[C@H:18]5[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21][CH2:20][CH2:19]5)[n:15][cH:14][cH:13][cH:12]1

Participants

9

Reactant 2

HCID 122032083-Bromopyrazolo(1,5-a)pyrimidineHCID 123439813Tert-butyl (R)-3-(N-(3-methylpyridin-2-YL)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzamido)piperidine-1-carboxylate

Product 1

HCID 117652897(R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 6

HCID 962WaterReagentHCID 10340Sodium CarbonateReagentHCID 167845palladium(II) acetateCatalystHCID 178454858HCID 178454858, compoundCatalystHCID 887MethanolSolventHCID 117669-PhenylanthraceneInternal standard

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-1bd69f9edd3549958c6183a9e6e5b706
Source dataset
39k HTE dataset from Pfizer
Original link
View source

Reaction notes

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