Formaldehyde → HCID 69712223, compound

HRID 2121911Notes

Reaction equation

HRID 2121911 reaction equation
[Si:1]([O:8][C@H:9]([CH3:21])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[CH:13]=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C=O.[OH-].[Na+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].[C:35](=O)(O)[O-:36].[Na+]>CN(C=O)C>[C:31]([O:30][C:28](=[O:29])[CH2:27][O:20][C:17]1[C:18]([CH2:35][OH:36])=[C:19]2[C:14]([CH:13]=[N:12][N:11]2[CH2:10][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH3:21])=[CH:15][CH:16]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 136477662HCID 136477662, compound

Product 1

HCID 69712223HCID 69712223, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-[(R)-2-(tert-Butyldimethylsilanyloxy)-propyl]-1H-indazol-6-ol (3.06 g, 10 mmol) in DMF (60 mL) was added formaldehyde (37%, 2.43 mL, 30 mmol) and 2 N NaOH (10 mmol). The mixture was stirred overnight and t-butyl bromoacetate (2.42 mL, 2.93 g, 15 mmol) was added. After 1 h the mixture was mixed with a saturated aqueous solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate. Chromatography on silica (gradient, 5% to 25% ethyl acetate in hexane) gave an oil (2.87 g, 64%): LC/MS (+APCI) m/z 451(M+H).

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-54603a93d1c743c59713c7eb221c1a34
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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