Sodium borohydride → HCID 25120909, compound

HRID 1640930Notes

Reaction equation

HRID 1640930 reaction equation
[Te].[BH4-].[Na+].[N:4]([CH:7]([C:9]1[C:10]([C:16]2[C:21]3[S:22][C:23]([C:25]4[C:30]([F:31])=[CH:29][N:28]=[C:27]([NH:32][CH2:33][CH2:34][N:35]5[CH:39]=[CH:38][N:37]=[N:36]5)[N:26]=4)=[CH:24][C:20]=3[CH:19]=[CH:18][CH:17]=2)=[CH:11][C:12]([F:15])=[N:13][CH:14]=1)[CH3:8])=[N+]=[N-]>C(O)C>[N:35]1([CH2:34][CH2:33][NH:32][C:27]2[N:26]=[C:25]([C:23]3[S:22][C:21]4[C:16]([C:10]5[C:9]([CH:7]([NH2:4])[CH3:8])=[CH:14][N:13]=[C:12]([F:15])[CH:11]=5)=[CH:17][CH:18]=[CH:19][C:20]=4[CH:24]=3)[C:30]([F:31])=[CH:29][N:28]=2)[CH:39]=[CH:38][N:37]=[N:36]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 86641881HCID 86641881, compound

Product 1

HCID 25120909HCID 25120909, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Combine tellurium (1.27 g, 10 mmol) and sodium tetrahydroborate (0.9 g, 2.4 mmol) in ethanol (20 mL) under nitrogen. Heat the mixture to refluxing until it becomes a clear red solution. Add 5 mL of the solution to a solution of (4-{7-[5-(1-azido-ethyl)-2-fluoro-pyridin-4-yl]-benzo[b]thiophen-2-yl}-5-fluoro-pyrimidin-2-yl)-(2-[1,2,3]-triazol-1-yl-ethyl)-amine (400 mg, 0.8 mmol) in ethanol (10 mL). Stir the mixture for 20 min at RT. Filter off the black solid. Wash the solid with methanol and DCM. Evaporate the combined mother liquor to give the crude product. Purify the crude product by FCC (chloroform/methanol/ammonium hydroxide, 7/3/0.05) to give the title compound as a yellow solid (200 mg, 52%). MS (ES) m/z 479 [M+1]+.

Workup

  1. temperatureHeat the mixture
  2. temperatureto refluxing until it
  3. filtrationFilter off the black solid
  4. washWash the solid with methanol and DCM
  5. customEvaporate the combined mother liquor
  6. customto give the crude product
  7. customPurify the crude product by FCC (chloroform/methanol/ammonium hydroxide, 7/3/0.05)

Sources & evidence

ORD record
ord-01c208525e38411dacd848a9fd975fc2
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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