Sodium Dithionite → Methyl 2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carboxylate

HRID 2275024Notes

Reaction equation

HRID 2275024 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([N+:23]([O-])=O)[C:20]=1[NH:21][CH3:22])[C:14]([O:16][CH3:17])=[O:15].[CH:26]1([CH2:29][N:30]2[C:34]3=[N:35][CH:36]=[CH:37][CH:38]=[C:33]3[CH:32]=[C:31]2[CH:39]=O)[CH2:28][CH2:27]1>O.C(O)C.C(Cl)Cl>[CH:26]1([CH2:29][N:30]2[C:34]3=[N:35][CH:36]=[CH:37][CH:38]=[C:33]3[CH:32]=[C:31]2[C:39]2[N:21]([CH3:22])[C:20]3[C:11]([O:10][CH3:9])=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][C:19]=3[N:23]=2)[CH2:27][CH2:28]1

Participants

7

Reactant 3

HCID 24489Sodium DithioniteHCID 86340167HCID 86340167, compoundHCID 86340173HCID 86340173, compound

Product 1

HCID 86340160Methyl 2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carboxylateYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of sodium hydrosulfite (512 mg, 2.498 mmol) in water (3.25 mL) was added to a solution of methyl 3-methoxy-4-(methylamino)-5-nitrobenzoate (200 mg, 0.833 mmol) and 1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (167 mg, 0.833 mmol) in ethanol (6.5 mL) in a microwave vial. The reaction mixture was heated in the microwave for 5 h at 100° C. The reaction mixture was diluted with DCM (20 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford the crude product as a colourless oil. The crude product was purified by column chromatography on a silica cartridge (25 g) using a gradient of 60% EtOAc/cyclohexane→100% EtOAc/cyclohexane. (The product eluted near the solvent front). The appropriate fractions were combined and evaporated under vacuum to give the product as a yellow oil—methyl 2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carboxylate (260 mg, 0.666 mmol, 80% yield)

Workup

  1. dry with materialdried (Na2SO4)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product as a colourless oil
  5. customThe crude product was purified by column chromatography on a silica cartridge (25 g)
  6. wash(The product eluted near the solvent front)
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-10071e16de8d48c7987d2ef32f98d225
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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