Cesium carbonate → HCID 118290299, compound

HRID 57134Notes

Reaction equation

HRID 57134 reaction equation
[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[N:31]=[CH:30][N:29]=[C:28]([NH2:32])[C:27]=3Br)[CH2:22][CH2:21]2)[CH2:4][CH2:3][CH2:2]1.[C:34]([O:38][C:39]([N:41]1[C:45](B2OC(C)(C)C(C)(C)O2)=[CH:44][CH:43]=[N:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].C([O-])([O-])=O.[Cs+].[Cs+]>>[C:34]([O:38][C:39]([N:41]1[C:45]([C:27]2[C:28]([NH2:32])=[N:29][CH:30]=[N:31][C:26]=2[N:23]2[CH2:24][CH2:25][CH:20]([C:8]3[N:7]([CH2:6][CH2:5][N:1]4[CH2:4][CH2:3][CH2:2]4)[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=4)[N:9]=3)[CH2:21][CH2:22]2)=[CH:44][CH:43]=[N:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 53217114Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazole-1-carboxylateHCID 89442737HCID 89442737, compound

Product 1

HCID 118290299HCID 118290299, compound

Conditions

Temperature
50 °C

Procedure

The mixture of 6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-bromo-pyrimidin-4-ylamine (90.00 mg; 0.17 mmol; 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (61.75 mg; 0.21 mmol; and Cs2CO3 (114.00 mg; 0.35 mmol; in dioxane (5 ml) and water (0.5 ml) was purged with argon, and then added Pd (0) (t-Bu3)2 (6.26 mg; 0.01 mmol; 0.07 eq.). The resulting mixture was stirred at 50° C. overnight. The curde was purified by prep HPLC to afford the title compound.

Workup

  1. customin dioxane (5 ml) and water (0.5 ml) was purged with argon
  2. customThe curde was purified by prep HPLC

Sources & evidence

ORD record
ord-25687ccc16fc4f179b882f04a6d19aa7
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

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