Potassium Carbonate → HCID 44250353, compound

HRID 1256299Notes

Reaction equation

HRID 1256299 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9](C)[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13](=[O:25])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:24])([CH3:23])[CH2:21]O)=[CH:16][CH:15]=2)[CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=2)=[O:25])=[CH:15][CH:16]=1)([CH3:21])([CH3:23])[CH3:24]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86652263HCID 86652263, compound

Product 1

HCID 44250353HCID 44250353, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide (4G, 44 mg, 1.0 equivalent), 4-fluorophenylboronic acid (1.2 equivalents), Pd(OAc)2 (0.05 equivalent), and K2CO3 (4.0 equivalents) in DME/H2O was warmed to 110° C. in a microwave reactor. The reaction mixture was cooled to room temperature, diluted with methanol, filtered, and purified via preparative HPLC to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.37 (s, 9 H) 6.50 (d, J=2.26 Hz, 1 H) 7.23-7.32 (m, 1 H) 7.56 (d, J=8.29 Hz, 2 H) 7.89 (d, J=8.29 Hz, 2 H) 8.11 (d, J=2.26 Hz, 1 H) 8.12-8.18 (m, 2 H) 8.25 (s, 1 H) 8.67 (s, 1 H); ESI-MS: m/z 389 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-9fb8ab6f26e34fa0aa03766d4a19a056
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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