Trimethyl orthoformate → HCID 59700612, compound

HRID 902023Notes

Reaction equation

HRID 902023 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)=[CH:6][C:3]=1[CH:4]=O.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30].C(OC)(OC)OC.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)=[CH:6][C:3]=1[CH2:4][NH:30][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 66053N,N-DimethylethylenediamineHCID 4311764Sodium borohydrideHCID 86600926HCID 86600926, compound

Product 1

HCID 59700612HCID 59700612, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-fluoro-5-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-benzaldehyde (0.05 g, 0.15 mmol), N,N-dimethyl-ethylenediamine (0.013 g, 0.15 mmol), trimethyl orthoformate (2 mL) in MeOH (5 mL) is stirred for 2 hours at room temperature. The reaction is then treated with sodium borohydride (6.8 mg, 0.18 mmol) and stirred overnight. The reaction is then quenched with 2N NaOH and stirred for 30 minutes. The solution is diluted in CH2Cl2 and washed with saturated aqueous NaHCO3, brine, and dried over sodium sulfate. The solvent is removed in vacuo to afford 0.06 g (100%) of desired product. MS ES+ m/e 404.1 (M+1).

Workup

  1. customThe reaction is then quenched with 2N NaOH
  2. stirringstirred for 30 minutes
  3. additionThe solution is diluted in CH2Cl2
  4. washwashed with saturated aqueous NaHCO3, brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c283b072b1104226ae86666828f8a67f
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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