Triphenylphosphine → 2-(4-{(1R,2S)-2-[2-(4-bromo-3-chlorophenoxy)ethyl]cyclopropyl}piperidin-1-yl)-5-(methoxymethyl)pyrimidine

HRID 1474688Notes

Reaction equation

HRID 1474688 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C@H:16]3[CH2:18][C@H:17]3[CH2:19][CH2:20][OH:21])[CH2:12][CH2:11]2)=[N:8][CH:9]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][C:24]=1[Cl:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([O:21][CH2:20][CH2:19][C@@H:17]2[CH2:18][C@@H:16]2[CH:13]2[CH2:14][CH2:15][N:10]([C:7]3[N:8]=[CH:9][C:4]([CH2:3][O:2][CH3:1])=[CH:5][N:6]=3)[CH2:11][CH2:12]2)=[CH:25][C:24]=1[Cl:30]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 70181824-Bromo-3-chlorophenolHCID 895817522-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethanol

Product 1

HCID 1176785802-(4-{(1R,2S)-2-[2-(4-bromo-3-chlorophenoxy)ethyl]cyclopropyl}piperidin-1-yl)-5-(methoxymethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethanol (670 mg, 2.30 mmol) was dissolved in toluene (5 ml) and 4-bromo-3-chlorophenol (525 mg, 2.53 mmol), triphenylphosphine (905 mg, 3.45 mmol), and DIAD (671 μl, 3.45 mmol) added and the mixture stirred at RT overnight. The mixture was concentrated in vacuo and the residue purified by column chromatography on SiO2 using a Biotage 50M cartridge using a gradient eluant of 0-50% EtOAc:hexanes to afford the title compound. LC/MS (m/z): 481 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by column chromatography on SiO2 using a Biotage 50M cartridge

Sources & evidence

ORD record
ord-142228065e424e45ab53ee8c5193adf3
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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