o-Fluorobenzaldehyde → HCID 86689211, compound

HRID 594936Notes

Reaction equation

HRID 594936 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([N:17]2[CH2:22][CH2:21][C:20]3[NH:23][N:24]=[C:25]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[C:19]=3[CH2:18]2)=[O:16])[CH2:9]1.[F:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Na]>C(O)(=O)C.ClCCl>[F:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH2:35][N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([N:17]2[CH2:22][CH2:21][C:20]3[NH:23][N:24]=[C:25]([C:26]4[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=4)[C:19]=3[CH2:18]2)=[O:16])[CH2:9]1

Participants

7

Reactant 4

HCID 67970o-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5360545SodiumHCID 86689212HCID 86689212, compound

Product 1

HCID 86689211HCID 86689211, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (0.295 mL) and acetic acid (2 drops) was added to N-(piperidin-3-yl)-3-(pyridin-4-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide trifluoroacetate salt (0.021 g, 0.05 mmol) and 2-fluorobenzaldehyde (0.0124 g, 0.1 mmol). The reaction was sonicated for 1 hr. Sodium triacetoxyborohydride (0.050 g, 0.25 mmol) was added in one portion. The reaction was stirred for an additional 16 hours. Saturated sodium bicarbarbonate (1 mL) was added. The reaction was stirred for an additional 5 minutes and was extracted with dichloromethane (3×1 mL). The extracts were combined, dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by prep LC/MS. LC-MS: 435.68 [M+H]. LC/MS RT=1.82 min.

Workup

  1. customThe reaction was sonicated for 1 hr
  2. stirringThe reaction was stirred for an additional 5 minutes
  3. extractionwas extracted with dichloromethane (3×1 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by prep LC/MS

Sources & evidence

ORD record
ord-0b233736ecec4724b6d0450a838e663f
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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