Triethylamine → HCID 58092314, compound

HRID 1918469Notes

Reaction equation

HRID 1918469 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:12][CH2:13][NH2:14])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][C:19](Cl)=O.CCN(CC)CC.O=P(Cl)(Cl)Cl.[BH4-].[Na+]>C(Cl)Cl.C1C=CC=CC=1.CCO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:12][CH2:13][N:14]4[CH:16]([CH2:17][CH2:18][CH2:19]4)[C:7]=3[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 702254-Bromobutyryl chlorideHCID 4311764Sodium borohydrideHCID 54594685HCID 54594685, compound

Product 1

HCID 58092314HCID 58092314, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(6-bromo-1-methyl-1H-indol-3-yl)ethanamine (6.50 g, 25.7 mmol) in CH2Cl2 (50 mL) were added 4-bromobutyryl chloride (4.50 mL, 38.6 mmol) and NEt3 (7.20 mL, 51.4 mmol). After 2 h, the reaction mixture was diluted with CH2Cl2 and filtered through a layer of Celite. The filtrate was concentrated to give a brown oil. The oil was diluted with benzene (120 mL) and treated with POCl3 (12 mL, 0.13 mol). The reaction mixture was heated at reflux for 1 h. After the mixture was concentrated, the residue was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2) to give the crude product (6.1 g) as a brown oil. The oil was diluted with EtOH and cooled to 0° C. NaBH4 (0.60 g, 16 mmol) was added, and the reaction was stirred from 0° C. to room temperature for 1 h. After the solution was concentrated, the residue was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2) to give the title compound (1.66 g, 34% in three steps) as a yellow foam: 1H NMR (300 MHz, CDCl3) δ 7.45 (d, J=1.5 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.23 (dd, J=8.4, 1.5 Hz, 1H), 4.79 (t, J=6.6 Hz, 1H), 3.63 (s, 3H), 3.44-3.25 (m, 3H), 3.16-3.10 (m, 1H), 2.99-2.96 (m, 2H), 2.70-2.61 (m, 1H), 2.26-1.96 (m, 3H); ESI MS m/z 305 [M+H]+.

Workup

  1. filtrationfiltered through a layer of Celite
  2. concentrationThe filtrate was concentrated
  3. customto give a brown oil
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 1 h
  6. concentrationAfter the mixture was concentrated
  7. customthe residue was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2)
  8. customto give the crude product (6.1 g) as a brown oil
  9. concentrationAfter the solution was concentrated
  10. customthe residue was purified by flash column chromatography (silica gel, 10% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-69bb95eba70f41f48e86d54f9a4a8585
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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