4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 66750277, compound

HRID 75437Notes

Reaction equation

HRID 75437 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:5]=[C:4]([CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1>>[CH:10]12[O:15][CH:13]([CH2:12][CH2:11]1)[CH2:14][N:8]([C:6]1[CH:5]=[C:4]([CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([NH2:21])=[CH:23][CH:24]=3)[N:7]=1)[CH2:9]2

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 866658953-(2-Chloro-6-(methylsulfonylmethyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 66750277HCID 66750277, compound

Procedure

4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)aniline was prepared by Suzuki coupling using the general method from scheme 2 for the preparation of 6 using 3-(2-chloro-6-(methylsulfonylmethyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (43, 1.63 g, 5.13 mmoles) and 4-aminophenyl boronic acid pinacol ester (1.24 g, 5.64 mmoles) as starting materials. The crude product was purified by chromatography on silica gel (eluting with 0-3% methanol in dichloromethane) to provide the desired compound as a light yellow solid. Yield: 1.80 g (94%). HRMS; [M+H]+ Obs'd=375.1485, [M+H]+ Calc'd=375.1485

Workup

  1. custom4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)aniline was prepared by Suzuki coupling
  2. customThe crude product was purified by chromatography on silica gel (eluting with 0-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e39fd4ebcf924b2e92467cade9f45e67
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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