Cesium carbonate → HCID 90303551, compound

HRID 1051926Notes

Reaction equation

HRID 1051926 reaction equation
Cl[C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH:7]([O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH2:8][CH2:9][OH:10].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>CC1C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[O:11][CH:7]1[C:6]2[S:5][CH:4]=[N:3][C:2]=2[O:10][CH2:9][CH2:8]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 90303201HCID 90303201, compound

Product 1

HCID 90303551HCID 90303551, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A soln. of 3-(4-chlorothiazol-5-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol (520 mg, 1.87 mmol) in MePh (10 mL) was added to a Ar-filled vial charged with Pd(OAc)2 (63 mg, 0.28 mmol), 2-(di-tert-butylphosphino)-1,1′-binaphthyl (140 mg, 0.35 mmol) and (Cs2CO3 915 mg, 2.81 mmol). The vial was sealed and placed in a preheated oilbath (100° C.) overnight. Subsequently, the mixture was diluted with DCM, filtrated over Celite, and conc. in vacuo. Purification by means of CC (20-80% EtOAc/Hept) provided the product as a yellow oil as an isomeric mixture.

Workup

  1. customThe vial was sealed
  2. customplaced in a preheated oilbath (100° C.) overnight
  3. filtrationfiltrated over Celite
  4. customPurification by means of CC (20-80% EtOAc/Hept)

Sources & evidence

ORD record
ord-690455e6291248b183986b317d48d023
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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