Diisopropylethylamine → 5-Bromo-2-[1-(5-fluoropyrimidin-2-yl)piperidin-4-yl]benzo[d]oxazole

HRID 710081Notes

Reaction equation

HRID 710081 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:16]=1.Cl[C:18]1[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=1.C(N(CC)C(C)C)(C)C.CCOC(C)=O.O>C(O)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:11][CH2:12][N:13]([C:18]4[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=4)[CH2:14][CH2:15]3)=[N:7][C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5834662-Chloro-5-fluoropyrimidineHCID 22728543Water ethylacetateHCID 711141905-Bromo-2-(piperidin-4-yl)benzo[d]oxazole

Product 1

HCID 712572725-Bromo-2-[1-(5-fluoropyrimidin-2-yl)piperidin-4-yl]benzo[d]oxazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

Intermediate 5 (1 g, 3.4 mmol) and 2-Chloro-5-fluoropyrimidine was dissolved in isopropanol (20 ml) and added N,N-diisopropylethyl amine (2.4 ml). This mixture was stirred at 90° C. for 90 mins. Isopropanol was removed on rotavapour to obtain a residue. Work up (EtOAc/H2O) followed by purification on combiflash using a gradient mixture of EtOAc and Petether (7:93) as eluent afforded the titled compound as a pink solid.

Workup

  1. customIsopropanol was removed on rotavapour
  2. customto obtain a residue
  3. customfollowed by purification on combiflash
  4. additiona gradient mixture of EtOAc and Petether (7:93) as eluent

Sources & evidence

ORD record
ord-69494ba41ebb41318f8b89c386389f2c
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

Loading…