Cesium carbonate → HCID 86613830, compound

HRID 2075712Notes

Reaction equation

HRID 2075712 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([Cl:13])[CH:7]=[CH:6]2.[F:14][C:15]1[CH:16]=[C:17]([OH:29])[CH:18]=[C:19]([C:21]2([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N.CCOC(C)=O.O>[Cl:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][O:29][C:17]3[CH:18]=[C:19]([C:21]4([O:27][CH3:28])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:20]=[C:15]([F:14])[CH:16]=3)[CH:4]=2)[N:9]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 112768896-(Bromomethyl)-2-chloroquinolineHCID 117362763-Fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenol

Product 1

HCID 86613830HCID 86613830, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromomethyl-2-chloro-quinoline (2.5 g, 9.7 mmol), 3-fluoro-5-(4-methoxy-tetrahydro-pyran-4-yl)-phenol (9a, 2.2 g, 9.7 mmol), and cesium carbonate (4.7 g, 14.6 mmol) were combined in MeCN (25 mL) and stirred at room temperature for 2 hours. The reaction was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the desired product, 9b.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a950d563f5549c3a71cb4b6198c0479
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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