3-Iodo-N-methoxy-N-methylbenzamide → (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone

HRID 916766Notes

Reaction equation

HRID 916766 reaction equation
[Li]CCCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:8]=1.[I:22][C:23]1[CH:24]=[C:25]([CH:32]=[CH:33][CH:34]=1)[C:26](N(OC)C)=[O:27]>C1COCC1>[Cl:16][C:14]1[C:15]2[C:7]([C:26]([C:25]3[CH:32]=[CH:33][CH:34]=[C:23]([I:22])[CH:24]=3)=[O:27])=[CH:8][N:9]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 223220523-Iodo-N-methoxy-N-methylbenzamideHCID 865964995-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 86760548(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanoneYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (3.65 mL, 2.5 M in hexanes, 9.14 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 8.31 mmol) in THF (50 mL) at −78° C. After 30 min a solution of 3-Iodo-N-methoxy-N-methyl-benzamide (2.29 g, 7.8 mmol) in THF (10 mL) was added. After 30 min the reaction was quenched with water and allowed to warm to room temperature. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with water and dried over Na2SO4. Recrystallization from MeOH afforded the title compound as a white solid (1.74 g, 49%). MS: 451.9/453.9 (MH+); HPLC Rf: 7.44 min. (HPLC method 4).

Workup

  1. customAfter 30 min the reaction was quenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-b9c4470565fb46849f2ba0a6a73d11af
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

Loading…