4-Fluorobenzaldehyde → HCID 57973859, compound

HRID 1864786Notes

Reaction equation

HRID 1864786 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[NH:36][CH:35]=[CH:34]3)=[CH:27][C:17]=1[CH2:18][NH:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1.[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=1.C(=O)(O)[O-].[Na+]>ClCCCl.ClCCl.C(O)(=O)C>[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][N:19]([CH2:18][C:17]2[CH:27]=[C:28]([C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[NH:36][CH:35]=[CH:34]4)[CH:29]=[CH:30][C:16]=2[F:15])[CH:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)=[CH:43][CH:42]=1

Participants

8

Reactant 4

HCID 680234-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68749600HCID 68749600, compound

Product 1

HCID 57973859HCID 57973859, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (470 mg, 2.23 mmol) and then enough acetic acid to bring the pH to 5 were added to a solution of [2-fluoro-5-(1H-indol-5-yl)-benzyl]-(1-methyl-piperidin-4-yl)-amine (250 mg, 0.74 mmol) and 4-fluorobenzaldehyde (183 mg, 1.48 mmol) in 15 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with dichloromethane, and neutralized with the careful addition of saturated sodium bicarbonate solution. The organic phase was separated and dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/ethyl acetate) provided 232 mg of product. LC/MS (long run): Retention time, 6.12 min; (M+H)=446.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto leave the crude product
  6. washChromatography (elution with methanol/ethyl acetate)

Sources & evidence

ORD record
ord-dd1ce86ac3a94464af934482d2427e88
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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