HCID 59394648, compound → HCID 59394346, compound

HRID 884571Notes

Reaction equation

HRID 884571 reaction equation
C([O:8][CH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]2[C:18]([F:27])=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([CH3:26])=[CH:20]3)[CH:11]=1)C1C=CC=CC=1>CS(O)(=O)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:27][C:18]1[C:17]([O:16][C:12]2[N:13]=[CH:14][N:15]=[C:10]([CH2:9][OH:8])[CH:11]=2)=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[C:21]([CH3:26])[NH:22]2

Participants

5

Reactant 1

HCID 59394648HCID 59394648, compound

Product 1

HCID 59394346HCID 59394346, compound

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

In a 20 mL microwave vial is placed 5-(6-benzyloxymethyl-pyrimidin-4-yloxy)-4-fluoro-2-methyl-1H-indole (2.59 g, 7.13 mmol) in methane sulfonic acid (15 ml) and the solution is heated in a microwave reactor at 100° C. for 5 min. The reaction is then diluted with 250 mL EtOAc and saturated aqueous NaHCO3. The aqueous layer is washed with EtOAc (4×100 mL). The organic phases are combined, washed with (2×150 mL) water, followed by (1×60 mL brine), dried over Na2SO4, and concentrated in vacuo. The residue is purified via FCC (0-20% MeOH/DCM) to give the title compound. MS (ESI) m/z 274.1 (M+1).

Workup

  1. washThe aqueous layer is washed with EtOAc (4×100 mL)
  2. washwashed with (2×150 mL) water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified via FCC (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-55fa06ce73544df7be494fa004d0de20
Source dataset
uspto-grants-2012_08
Patent number
US08242125B2

Reaction notes

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