Formaldehyde → HCID 59463923, compound

HRID 2387641Notes

Reaction equation

HRID 2387641 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:25]([C:26]2[S:27][C:28]3[CH2:29][NH:30][CH2:31][CH2:32][C:33]=3[N:34]=2)[N:24]=[C:23]([C:35]2[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=2[F:42])[S:22]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C=O.[C:51](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[F:42][C:36]1[CH:37]=[CH:38][C:39]([F:41])=[CH:40][C:35]=1[C:23]1[S:22][C:21]([CH2:20][CH2:19][OH:18])([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:25]([C:26]2[S:27][C:28]3[CH2:29][N:30]([CH3:51])[CH2:31][CH2:32][C:33]=3[N:34]=2)[N:24]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68500709HCID 68500709, compound

Product 1

HCID 59463923HCID 59463923, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Preparation of 2-(2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-[2,5-c]pyridine: To a solution of 2-(2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (0.157 g, 0.225 mmol) in 5 mL DCE was added formaldehyde (0.067 mL, 37 wt % in water, 0.901 mmol) followed by sodium triacetoxyborohydride (0.052 g, 0.248 mmol). The resulting suspension was stirred vigorously at room temperature overnight, then treated with saturated Na2CO3 solution (30 mL) and stirred for 10 minutes. The mixture was extracted with EtOAc (3×30 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (0-1% MeOH/DCM) to afford the desired product as a bright yellow foam, 0.119 g, 74%.

Workup

  1. stirringstirred for 10 minutes
  2. extractionThe mixture was extracted with EtOAc (3×30 mL)
  3. washthe combined organic phases were washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (0-1% MeOH/DCM)

Sources & evidence

ORD record
ord-cc0ddf6f1f1f4ab79158037e9210e7c8
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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