Formaldehyde → HCID 118524066, compound

HRID 531530Notes

Reaction equation

HRID 531530 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)[CH:21]=4)[CH:18]=3)[N:13]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:12]=2)[CH:8]=[N:7]1.C=O.[C:47](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:27][CH2:28][N:29]([CH3:47])[CH2:30][CH2:31]5)[CH:21]=4)[CH:18]=3)[N:13]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:33])=[O:34])[CH:12]=2)[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 90031181HCID 90031181, compound

Product 1

HCID 118524066HCID 118524066, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step-i of example-35) (87 mg, 0.143 mmol), HCHO (13 mg, 0.43 mmol), 1,2-dichloroethane (2 ml) was stirred at RT under nitrogen for 30 minutes. Sodium triacetoxy borohydride (91 mg, 0.43 mmol) was then added and stirred at the same temperature for overnight. Reaction mass quenched water, basified by saturated sodium bicarbonate and extracted into ethyl acetate. Organic layer dried over sodium sulfate and concentrated to give 74 mg (84% yield) of the titled compound. MS: m/z=621.0 (M+1).

Workup

  1. stirringstirred at the same temperature for overnight
  2. customReaction mass
  3. customquenched water
  4. extractionextracted into ethyl acetate
  5. dry with materialOrganic layer dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ec85bd9bece4135808b2cae5497add5
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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