Methanol → HCID 86720157, compound

HRID 2408586Notes

Reaction equation

HRID 2408586 reaction equation
COC(=O)[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([O:25][C:26]5[CH:31]=[CH:30][C:29](I)=[CH:28][N:27]=5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[C:34]([O-:37])([O-])=[O:35].[Cs+].[Cs+].CC1C(C)=CC2C(=C3C(=CC=2)C(C)=C(C)C=N3)N=1.[OH-:58].[Na+].[CH3:60]O>[Cu]I.O.C1(C)C=CC=CC=1>[F:24][C:22]1[CH:21]=[CH:20][C:19]([O:25][C:26]2[CH:31]=[CH:30][C:29]([O:58][CH3:60])=[CH:28][N:27]=2)=[C:18]2[C:23]=1[C@H:15]([O:14][C:12]1[CH:11]=[CH:10][C:9]3[C@H:5]([CH2:4][C:34]([OH:37])=[O:35])[CH2:6][O:7][C:8]=3[CH:13]=1)[CH2:16][CH2:17]2

Participants

9

Reactant 5

HCID 887MethanolHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 19101362HCID 19101362, compoundHCID 86720134HCID 86720134, compound

Product 1

HCID 86720157HCID 86720157, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Methanol (24 μL) is added to a flask charged with a stir bar, {(S)-6-[(R)-7-fluoro-4-(5-iodo-pyrid-2-yloxy)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (60 mg), CuI (1 mg), Cs2CO3 (52 mg), 2,3,7,8-tetramethyl-1,10-phenanthroline (2.5 mg) and toluene (2 mL) under Ar atmosphere at room temperature. The flask is sealed and heated to 120° C., and the mixture is stirred at this temperature overnight. After cooling to room temperature, 4 M aqueous NaOH solution (50 μL) is added and the mixture is stirred for 4 h. Water is added, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4) and concentrated. The residue is purified by HPLC (water/acetonitrile/trifluoroacetic acid) to give the title compound. LC (method 6): tR=1.06 min; Mass spectrum (ESI+): m/z=452 [M+H]+.

Workup

  1. additioncharged with a stir bar
  2. customat room temperature
  3. customThe flask is sealed
  4. temperatureAfter cooling to room temperature
  5. stirringthe mixture is stirred for 4 h
  6. extractionthe resulting mixture is extracted with ethyl acetate
  7. extractionThe combined extract
  8. washis washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customThe residue is purified by HPLC (water/acetonitrile/trifluoroacetic acid)

Sources & evidence

ORD record
ord-cf9a8104a0184298afc8b3aa850be0a4
Source dataset
uspto-grants-2014_08
Patent number
US08815864B2

Reaction notes

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