Sodium triacetoxyborohydride → 4-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline

HRID 512831Notes

Reaction equation

HRID 512831 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.[CH3:11][N:12]1[CH:16]=[C:15]([C:17]2[N:22]=[N:21][C:20]([N:23]3[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH:14]=[N:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[CH:26]1[CH2:27][CH2:28][N:23]([C:20]2[N:21]=[N:22][C:17]([C:15]3[CH:14]=[N:13][N:12]([CH3:11])[CH:16]=3)=[CH:18][CH:19]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 162444404-Fluoro-2,3-dihydro-1H-indoleHCID 896139951-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-one

Product 1

HCID 763291794-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-fluoroindoline (62 mg, 0.45 mmol) and 1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-one, prepared as in STEP 3 above (77 mg, 0.3 mmol) in CH2Cl2 (3 mL) was added NaBH(OAc)3 (126 mg, 0.6 mmol). The resulting mixture was stirred at room temperature for 24 h and then concentrated. The resulting mixture was purified by column using 90-100% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to yield the 4-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline as a residue. The title compound was then converted to its corresponding HCl salt.

Workup

  1. concentrationconcentrated
  2. customThe resulting mixture was purified by column

Sources & evidence

ORD record
ord-a89d20bebbee4bc8977e6f3e894b23c7
Source dataset
uspto-grants-2015_08
Patent number
US09102669B2

Reaction notes

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