Methanol → (3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol

HRID 588108Notes

Reaction equation

HRID 588108 reaction equation
[CH2:1]([O:8][C:9]1[C:13]2[C:14]([CH:19]=[O:20])=[N:15][C:16]([Cl:18])=[CH:17][C:12]=2[N:11]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:13]2[C:14]([CH2:19][OH:20])=[N:15][C:16]([Cl:18])=[CH:17][C:12]=2[N:11]([C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 1182717453-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

Product 1

HCID 118271865(3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (2.8884 g, 5.45 mmol) in DCM (10 ml) was charged with MeOH (20 ml) and then sodium borohydride (0.309 g, 8.17 mmol). Stirred at RT for 2 hr. Quenched with water and extracted into DCM. Dried organics over MgSO4, filtered, concentrated in vacuo and used as-is. MS: [M+H]+ m/z 532.

Workup

  1. customQuenched with water
  2. extractionextracted into DCM
  3. filtrationDried organics over MgSO4, filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf8d9dee2997402ebc0a8a6b18dc0315
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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