Acetic Acid → 1-(2-chlorophenyl)-5-(4-fluorobenzyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1 H-pyrrolo-[3,2-c]pyridine

HRID 1790035Notes

Reaction equation

HRID 1790035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][N:13]([CH2:30][C:29]3[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=3)[CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 220385001-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 101845091-(2-chlorophenyl)-5-(4-fluorobenzyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1 H-pyrrolo-[3,2-c]pyridineYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 677.7 mg, 0.50 mmol), 4-fluorobenzaldehyde (0.13 mL, 0.60 mmol), acetic acid (0.03 mL, 0.60 mmol), and NaBH(OAc)3 (148.4 mg, 0.70 mmol) in methylene chloride (15 mL) was stirred at rt for 24 h. Sodium hydroxide (1N) was added, and the solution was extracted with diethyl ether (3×30 mL). The combined ether layers were dried (sodium sulfate), filtered, and evaporated. The residue was purified by silica gel column, eluting with 3:1 hexanes:ethyl acetate. The product was isolated as a white solid (218.1 mg, 97%). LC-MS m/z (MH+) 447, retention time 2.65 min (method 1).

Workup

  1. extractionthe solution was extracted with diethyl ether (3×30 mL)
  2. dry with materialThe combined ether layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel column
  6. washeluting with 3:1 hexanes

Sources & evidence

ORD record
ord-59c2d44fd8294022b89c4269dbe6bbe8
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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