Formaldehyde → HCID 118060296, compound

HRID 2274839Notes

Reaction equation

HRID 2274839 reaction equation
Cl.[F:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:25]=3)=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.[CH3:32]CN(CC)CC.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[F:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH:25]=3)=[CH:8][N:9]2[S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 1180603056-fluoro-1-(phenylsulfonyl)-3-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-indole hydrochloride2×

Product 1

HCID 118060296HCID 118060296, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-fluoro-1-(phenylsulfonyl)-3-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-indole hydrochloride (Intermediate 17; 290 mg), Et3N (55 mg; 0.55 mmol)cOH (1 drop), and 37% aqueous HCHO (89 mg; 1.1 mmol) in MeOH (10 mL) was added NaBH(OAc)3 (233 mg; 1.05 mmol). The reaction mixture was stirred for 16 h and concentrated. The residue was dissolved in DCM (20 mL) and washed with saturated NaHCO3 (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford 270 mg (>100%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM (20 mL)
  3. washwashed with saturated NaHCO3 (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1424fcd772cc4d18b071a9debefe91df
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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