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 → 4-[4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

HRID 133054Notes

Reaction equation

HRID 133054 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:40]=[C:14]3[N:15](CC4C=CC(OC)=CC=4)[CH:16]=[N:17][C:18]([O:19][C:20]4[C:21]([F:30])=[C:22]5[C:26](=[CH:27][CH:28]=4)[NH:25][C:24]([CH3:29])=[CH:23]5)=[C:13]3[CH:12]=2)=[CH:7][CH:6]=1)[CH3:2]>C1COCC1.CN1CCN(C)C1=O.[Pd]>[CH2:1]([O:3][C:4](=[O:41])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:40][C:14]3[N:15]=[CH:16][N:17]=[C:18]([O:19][C:20]4[C:21]([F:30])=[C:22]5[C:26](=[CH:27][CH:28]=4)[NH:25][C:24]([CH3:29])=[CH:23]5)[C:13]=3[CH:12]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 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

Product 1

HCID 691794854-[4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenation of 0.50 g (0.91 mMol) of 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 in 150 ml of THF and 15 ml of 1,3-dimethyl-2-imidazolidinone in the presence of 0.2 g of Pd/C (10%; “Engelhard 5125”), filtration and concentration gives the crude product. Stirrng in THF/water, filtration and washing with water gives the title compound; MS-ES+: (M+H)+=431; elemental analysis for C, H, N, and ,F within 0.4%; of calculated value.

Workup

  1. customgives the crude product
  2. filtrationStirrng in THF/water, filtration
  3. washwashing with water

Sources & evidence

ORD record
ord-ed31eb1fb9c14087a5ce7602558f9e22
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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