Potassium Carbonate → 4-[4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

HRID 133053Notes

Reaction equation

HRID 133053 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:29]=[C:14]3[N:15]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[CH:16]=[N:17][C:18](Cl)=[C:13]3[CH:12]=2)=[CH:7][CH:6]=1)[CH3:2].[F:31][C:32]1[C:40]([OH:41])=[CH:39][CH:38]=[C:37]2[C:33]=1[CH:34]=[C:35]([CH3:42])[NH:36]2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:29]=[C:14]3[N:15]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[CH:16]=[N:17][C:18]([O:41][C:40]4[C:32]([F:31])=[C:33]5[C:37](=[CH:38][CH:39]=4)[NH:36][C:35]([CH3:42])=[CH:34]5)=[C:13]3[CH:12]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 865953384-[4-Chloro-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

Product 1

HCID 691806034-[4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3.96 g (9.4 mMol) of 4-[4-chloro-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester, 2.14 g (13 mMol) of 4-fluoro-5-hydroxy-2-methyl-1H-indole (preparation see WO 00/47212; Ex. 237) and 2.44 (17.7 mMol) of K2CO3 in 90 ml of DMF is heated for 9 h at 95° C. The reaction mixture is concentrated in vacuuo, the residue dissolved in EtOAc and water, the aqueous layer separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2, EtOAc/hexane 1:1) gives the title compound; TLC (EtOAc/hexane 1:1) Rf=0.24; MS-ES+: (M+H)+=551.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuuo
  2. dissolutionthe residue dissolved in EtOAc
  3. customwater, the aqueous layer separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88a8ce02d3d14030906d74368fdb295e
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

Loading…