o-Fluorobenzaldehyde → HCID 56941067, compound

HRID 1842048Notes

Reaction equation

HRID 1842048 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH:16][C:17]([CH:19]4[O:24][CH2:23][CH2:22][NH:21][CH2:20]4)=[O:18])[CH:14]=3)[NH:9][N:8]=2)=[CH:3][CH:2]=1.[F:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Na]>C(O)(=O)C.ClCCl>[F:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][N:21]1[CH2:22][CH2:23][O:24][CH:19]([C:17]([NH:16][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[NH:9][N:8]=[C:7]3[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[O:18])[CH2:20]1

Participants

7

Reactant 4

HCID 67970o-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5360545SodiumHCID 56941370HCID 56941370, compound

Product 1

HCID 56941067HCID 56941067, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (0.5 mL) and acetic acid (3drops) was added to N-(3-(pyridin-4-yl)-1H-indazol-5-yl)morpholine-2-carboxamide (0.014 g, 0.0443 mmol) and 2-fluorobenzaldehyde (0.0112 g, 0.09 mmol). The reaction was stirred for 15 minutes. Sodium triacetoxyborohydride (0.040 g, 0.177 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: 432.2 [M+H]. LC/MS RT0.869 min.

Workup

  1. stirringThe reaction was stirred for an additional 16 hours
  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-2273f8b794d9485caba75590d46699bb
Source dataset
uspto-grants-2015_02
Patent number
US08946216B2

Reaction notes

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