Sodium borohydride → (6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol

HRID 590831Notes

Reaction equation

HRID 590831 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]2[C:10]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[N:11][N:12]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[C:5]2[C:10]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[N:11][N:12]([C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1182722196-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

Product 1

HCID 118271519(6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

6-Chloro-3-morpholino-1-trityl-1H-pyrazolo [4,3-c]pyridine-4-carbaldehyde (292.2 mg, 0.574 mmol) was dissolved in DCM (3 mL) and methanol (3 mL). Sodium borohydride (21.72 mg, 0.574 mmol) was then added and the reaction mixture was stirred at rt for 15 min. The reaction was quenched with water and extracted with DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo while loading onto silica gel. Purification by flash chromatography (5-40% EtOAc/Hexanes) gave (6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol. MS ESI calc'd. For C30H28ClN4O2 [M+H]+ 511. found 511.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (5-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-5c51c03f63804ec1be8f4d45309bd289
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

Loading…