Sodium borohydride → HCID 71061313, compound

HRID 875452Notes

Reaction equation

HRID 875452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:29])[C:11]=1[C:12]([C:14]1[C:22]2[C:17](=[C:18]([NH:23][C:24]([CH:26]3[CH2:28][CH2:27]3)=[O:25])[N:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])[C:5](OC)=[O:6].[BH4-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[C:10]([Cl:29])[C:11]=1[C:12]([C:14]1[C:22]2[C:17](=[C:18]([NH:23][C:24]([CH:26]3[CH2:28][CH2:27]3)=[O:25])[N:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86720651HCID 86720651, compound

Product 1

HCID 71061313HCID 71061313, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoate (100 mg, 2.31 mmol) in 1,4-dioxane and water (3:1), sodium borohydride (27 mg, 6.944 mmol) was added portion wise over a period of about 15 minutes, followed by heating the reaction mixture at 60° C. until starting material was consumed (approximately 3 hours) The reaction mixture was cooled to room temperature and quenched by the addition of saturated aq. ammonium chloride solution and extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over sodium sulfate and concentrated under vacuum. Purification by silica gel (100-200) column chromatography using dichloromethane and methanol gradient as eluent afforded N-{3-[2,6-dichloro-4-(hydroxymethyl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropane carboxamide (20 mg, 22%).

Workup

  1. customwas consumed (approximately 3 hours) The reaction mixture
  2. temperaturewas cooled to room temperature
  3. customquenched by the addition of saturated aq. ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customPurification by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-c25363a611a6401f80f97b456af7277e
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

Loading…